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Journal articles on the topic 'Triplet Photosensitizers'

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Author: Grafiati

Published: 10 March 2023

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1

Wu, Xupeng, Zhirong Zhu, Zhenxing Liu, Xiangyu Li, Tijian Zhou, Xiaolei Zhao, Yuwei Wang, et al. "Tricyano-Methylene-Pyridine Based High-Performance Aggregation-Induced Emission Photosensitizer for Imaging and Photodynamic Therapy." Molecules 27, no. 22 (November 17, 2022): 7981. http://dx.doi.org/10.3390/molecules27227981.

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Photosensitizers equipped with high reactive oxygen species (ROS) generation capability and bright emission are essential for accurate tumor imaging and precise photodynamic therapy (PDT). However, traditional aggregation-caused quenching (ACQ) photosensitizers cannot simultaneously produce desirable ROS and bright fluorescence, resulting in poor image-guided therapy effect. Herein, we report an aggregation-induced emission (AIE) photosensitizer TCM-Ph with a strong donor–π–acceptor (D–π–A) structure, which greatly separates the HOMO–LUMO distribution and reduces the ΔEST, thereby increasing the number of triplet excitons and producing more ROS. The AIE photosensitizer TCM-Ph has bright near-infrared emission, as well as a higher ROS generation capacity than the commercial photosensitizers Bengal Rose (RB) and Chlorine e6 (Ce6), and can effectively eliminate cancer cells under image guidance. Therefore, the AIE photosensitizer TCM-Ph has great potential to replace the commercial photosensitizers.

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2

Mahammed, Atif, and Zeev Gross. "Corroles as triplet photosensitizers." Coordination Chemistry Reviews 379 (January 2019): 121–32. http://dx.doi.org/10.1016/j.ccr.2017.08.028.

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3

Wei, Yaxiong, Miaomiao Zhou, Qiaohui Zhou, Xiaoguo Zhou, Shilin Liu, Song Zhang, and Bing Zhang. "Triplet–triplet annihilation upconversion kinetics of C60–Bodipy dyads as organic triplet photosensitizers." Physical Chemistry Chemical Physics 19, no. 33 (2017): 22049–60. http://dx.doi.org/10.1039/c7cp03840b.

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4

Hasegawa, Ryohei, Shinji Iwakiri, and Yuji Kubo. "Synthesis and triplet sensitization of bis(arylselanyl)BOPHYs; potential application in triplet–triplet annihilation upconversion." New Journal of Chemistry 45, no. 13 (2021): 6091–99. http://dx.doi.org/10.1039/d1nj00721a.

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5

Yang, Zi-Shu, Yingying Ning, Hao-Yan Yin, and Jun-Long Zhang. "Lutetium(iii) porphyrinoids as effective triplet photosensitizers for photon upconversion based on triplet–triplet annihilation (TTA)." Inorganic Chemistry Frontiers 5, no. 9 (2018): 2291–99. http://dx.doi.org/10.1039/c8qi00477c.

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6

Guo, Song, Liang Xu, Kejing Xu, Jianzhang Zhao, Betül Küçüköz, Ahmet Karatay, Halime Gul Yaglioglu, Mustafa Hayvali, and Ayhan Elmali. "Bodipy–C60 triple hydrogen bonding assemblies as heavy atom-free triplet photosensitizers: preparation and study of the singlet/triplet energy transfer." Chemical Science 6, no. 7 (2015): 3724–37. http://dx.doi.org/10.1039/c4sc03865g.

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7

Wei, Yaxiong, Min Zheng, Lin Chen, Xiaoguo Zhou, and Shilin Liu. "Near-infrared to violet triplet–triplet annihilation fluorescence upconversion of Os(ii) complexes by strong spin-forbidden transition." Dalton Transactions 48, no. 31 (2019): 11763–71. http://dx.doi.org/10.1039/c9dt02276g.

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8

Peng, Jiang, Xinyan Guo, Xinpeng Jiang, Dahui Zhao, and Yuguo Ma. "Developing efficient heavy-atom-free photosensitizers applicable to TTA upconversion in polymer films." Chemical Science 7, no. 2 (2016): 1233–37. http://dx.doi.org/10.1039/c5sc03245h.

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9

Zhang, Caishun, and Jianzhang Zhao. "Triplet excited state of diiodoBOPHY derivatives: preparation, study of photophysical properties and application in triplet–triplet annihilation upconversion." Journal of Materials Chemistry C 4, no. 8 (2016): 1623–32. http://dx.doi.org/10.1039/c5tc03193a.

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10

Berhe, Seare A., Zachary B. Molinets, Maya N. Frodeman, Blair Miller, Vladimir N. Nesterov, Keith M. Haynes, Collin M. Perry, Marco T. Rodriguez, Roy N. McDougald, and W. Justin Youngblood. "Synthesis, photophysical characterization, and photoelectrochemical evaluation of a palladium porphyrin sensitizer for TiO2-based dye-sensitized solar cells." Journal of Porphyrins and Phthalocyanines 19, no. 09 (September 2015): 1021–31. http://dx.doi.org/10.1142/s1088424615500741.

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An unsymmetrical (A3B) palladium porphyrin bearing a cyanoacrylic acid at one meso position has been synthesized for evaluation as a photosensitizer in dye-sensitized solar cells based on titanium dioxide ( TiO 2) as a comparison to other metalloporphyrins and as a proxy for other potential triplet-state photosensitizer compounds. The synthesis of this palladium porphyrin has provided new insight into the mechanism and product distribution of decarboxylative hydrolysis of malonic acid when attached at the porphyrin meso position. A crystal structure determination for a meso-formyl palladium porphyrin has been determined, showing saddle-distortion of the porphyrin core. The photophysical behavior of the palladium porphyrin sensitizer and its performance in photoelectrochemical cells are described and interpreted in the context of bimolecular excited state quenching pathways including oxygen sensitization, triplet–triplet annihilation and electron transfer events. Palladium porphyrins are proposed as a sensitizer class with potential for high efficiency dye-sensitized solar cells, but with the caveat that some overpotential for electron injection is necessary to compete against the multiple decay pathways that are specially available to triplet state photosensitizers.

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11

Sakamoto, Keiichi, Eiko Ohno-Okumura, Taku Kato, Tomomi Kawaguchi, and Michael J. Cook. "Laser-flash photolysis of dialkylbenzodipyridoporphyrazines." Journal of Porphyrins and Phthalocyanines 07, no. 02 (February 2003): 83–88. http://dx.doi.org/10.1142/s1088424603000112.

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In the course of a fundamental study of photosensitizers for photodynamic therapy of cancer, a non-peripheral substituted phthalocyanine analogue, zinc bis(1,4-didecylbenzo)bis(3,4-pyrido)porphyrazine and its position isomers were examined to measure their photoexcited triplet state lifetimes in poly(methyl methacrylate) film using laser-flash photolysis. The isomer mixture of zinc bis(1,4-didecylbenzo)bis(3,4-pyrido)porphyrazine showed the most intense absorption in the 660-710 nm region, and the longer triplet state lifetime. The lowest symmetry isomer of zinc bis(1,4-didecylbenzo)bis(3,4-pyrido)porphyrazine was found to have the longest triplet state lifetime when all isomers were separated. The compound is proposed to be suitable for use as a photosensitizer for photodynamic therapy of cancer.

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12

Engel, Paul S., and Akihide Kitamura. "Quenching of triplet photosensitizers by ketenimines." Journal of Physical Chemistry 90, no. 9 (April 1986): 1928–31. http://dx.doi.org/10.1021/j100400a037.

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13

Nakashima, Mika, Keita Iizuka, Masanobu Karasawa, Kazuyuki Ishii, and Yuji Kubo. "Selenium-containing BODIPY dyes as photosensitizers for triplet–triplet annihilation upconversion." Journal of Materials Chemistry C 6, no. 23 (2018): 6208–15. http://dx.doi.org/10.1039/c8tc00944a.

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14

Zhang, Xian-Fu, Jingyao Huang, Qian Xi, and Yun Wang. "The Excited Triplet State Properties of Titanyl Phthalocyanine and its Sulfonated Derivatives." Australian Journal of Chemistry 63, no. 10 (2010): 1471. http://dx.doi.org/10.1071/ch10076.

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Titanyl phthalocyanine (TiOPc) is a well-known, excellent photoconductive material for laser printers and photocopying machines. Its organic derivatives have recently been shown to be excellent photosensitizers for singlet oxygen [O2(1Δg)] production. The excited triplet state properties of TiOPc, in homogeneous DMSO solution, were measured in this study for the first time by nanosecond laser flash photolysis. The data enabled comparisons to be drawn with TiOPcS4 and zinc phthalocyanine (ZnPc), ultimately providing a better understanding of the reported observations. Absorption, fluorescence, and O2(1Δg) sensitization were also studied. TiOPcS4 in DMSO shows remarkably different fluorescence properties from that reported in aqueous solution: both the fluorescence quantum yield (Φf = 0.068) and the fluorescence lifetime (τf = 3.71 ns) were much larger than that reported for aqueous solutions (0.012 and 0.09 ns, respectively). The photosensitizing properties of TiOPcS4 in DMSO are also so significantly better than that in aqueous solution, i.e. triplet lifetime (τT) of 252 μs, triplet quantum yield (ΦT) of 0.42, and the quantum yield of O2(1Δg) (ΦΔ) of 0.49; compare with values of 60 μs, 0.32, 0.13 reported in aqueous solution. TiOPc, however, shows comparable photophysical properties to that of ZnPc, a well-recognized photosensitizer. These results suggest that TiOPc and its derivatives are not only good photoconductors but also good photosensitizers of O2(1Δg), which may find application in photodynamic therapies for treatment of cancer.

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15

Wu, Wanhua, Jianzhang Zhao, Jifu Sun, and Song Guo. "Light-Harvesting Fullerene Dyads as Organic Triplet Photosensitizers for Triplet–Triplet Annihilation Upconversions." Journal of Organic Chemistry 77, no. 12 (May 30, 2012): 5305–12. http://dx.doi.org/10.1021/jo300613g.

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16

Nyokong, Tebello. "Desired properties of new phthalocyanines for photodynamic therapy." Pure and Applied Chemistry 83, no. 9 (June 12, 2011): 1763–79. http://dx.doi.org/10.1351/pac-con-10-11-22.

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The manuscript focuses on the properties of phthalocyanines (Pcs) that are required for them to be employed as photosensitizers in applications such as photodynamic therapy (PDT). High triplet-state quantum yields and lifetimes as well as high singlet-oxygen quantum yields are required for a good photosensitizer. In addition, absorption of the photosensitizer in the red region of the electromagnetic spectrum is also required, and this can be achieved by ring expansion, substitution with electron-donating ligands, and change of the central metal among others. Quantum dots (QDs) are efficient accumulators of light energy, and they can transfer this energy to molecules that possess a very efficient ability to generate singlet oxygen through a process called Förster resonance energy transfer (FRET). Thus, there is a decrease in the fluorescence quantum yield of the QDs when in the vicinity of Pcs. Triplet quantum yields of the Pcs increase in the presence of QDs.

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17

Pérez-Prieto, Julia, Lourdes Pastor Pérez, María González-Béjar, Miguel A. Miranda, and Salah-Eddine Stiriba. "Pyrene-benzoylthiophene bichromophores as selective triplet photosensitizers." Chemical Communications, no. 44 (2005): 5569. http://dx.doi.org/10.1039/b510880b.

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18

Zhao, Jianzhang, Wanhua Wu, Jifu Sun, and Song Guo. "Triplet photosensitizers: from molecular design to applications." Chemical Society Reviews 42, no. 12 (2013): 5323. http://dx.doi.org/10.1039/c3cs35531d.

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19

Xiao, Xiao, Kaiyue Ye, Muhammad Imran, and Jianzhang Zhao. "Recent Development of Heavy Atom-Free Triplet Photosensitizers for Photodynamic Therapy." Applied Sciences 12, no. 19 (October 2, 2022): 9933. http://dx.doi.org/10.3390/app12199933.

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Photodynamic therapy (PDT) is an attractive method for cancer treatment. Triplet photosensitizers (PSs) are critical for this method; upon photoexcitation, efficient intersystem crossing (ISC) occurs for triplet PSs, the triplet-excited state of the triplet PSs is populated, then via intermolecular triplet energy transfer, the O2, in triplet-spin multiplicity at ground state, is sensitized to the singlet-excited state, i.e., singlet oxygen (1O2) is produced. This strong reactive oxygen species (ROS) will oxidize the biomolecules in the tumor tissue. Thus, the design of novel triplet PSs as efficient PDT agents is vital. In this review article, we will introduce the recent development of the heavy atom-free triplet PSs used for PDT, including those based on spin-orbit charge transfer ISC (SOCT-ISC), twisting of the π-conjugation framework-induced ISC, radical enhanced ISC, and thionated carbonyl-induced ISC. The ISC mechanisms and molecular structure design rationales are discussed. The less studied electron spin selectivity of the ISC of the triplet PSs is also introduced. This information is helpful for the future design of new efficient triplet PSs for PDT.

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20

Zhang, Xian-Fu, Xudong Yang, and Baomin Xu. "PET-based bisBODIPY photosensitizers for highly efficient excited triplet state and singlet oxygen generation: tuning photosensitizing ability by dihedral angles." Physical Chemistry Chemical Physics 19, no. 36 (2017): 24792–804. http://dx.doi.org/10.1039/c7cp02645e.

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21

Huang, Dandan, Jifu Sun, Lihua Ma, Caishun Zhang, and Jianzhang Zhao. "Preparation of ketocoumarins as heavy atom-free triplet photosensitizers for triplet–triplet annihilation upconversion." Photochemical & Photobiological Sciences 12, no. 5 (2013): 872. http://dx.doi.org/10.1039/c3pp25416j.

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22

Arnaut, Luis G., and Sebastião J. Formosinho. "From elementary reactions to chemical relevance in the photodynamic therapy of cancer." Pure and Applied Chemistry 85, no. 7 (February 25, 2013): 1389–403. http://dx.doi.org/10.1351/pac-con-12-08-16.

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Theories of radiationless conversions and of chemical processes were employed to design better photosensitizers for photodynamic therapy (PDT). In addition to photostability and intense absorption in the near infrared, these photosensitizers were required to generate high yields of long-lived triplet states that could efficiently transfer their energy, or an electron, to molecular oxygen. The guidance provided by the theories was combined with the ability to synthesize large quantities of pure photosensitizers and with the biological screening of graded hydrophilicities/lipophilicities. The theoretical prediction that halogenated sulfonamide tetraphenylbacteriochlorins could satisfy all the criteria for ideal PDT photosensitizers was verified experimentally.

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23

Cui, Xiaoneng, Caishun Zhang, Kejing Xu, and Jianzhang Zhao. "Application of singlet energy transfer in triplet state formation: broadband visible light-absorbing triplet photosensitizers, molecular structure design, related photophysics and applications." Journal of Materials Chemistry C 3, no. 34 (2015): 8735–59. http://dx.doi.org/10.1039/c5tc01401h.

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24

Zhao, Jianzhang, Ling Huang, Xiaoneng Cui, Shujing Li, and Huijian Wu. "Maximizing the thiol-activated photodynamic and fluorescence imaging functionalities of theranostic reagents by modularization of Bodipy-based dyad triplet photosensitizers." Journal of Materials Chemistry B 3, no. 47 (2015): 9194–211. http://dx.doi.org/10.1039/c5tb01857a.

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25

Zhao, Jianzhang, Kepeng Chen, Yuqi Hou, Yuanyuan Che, Lang Liu, and Dianzeng Jia. "Recent progress in heavy atom-free organic compounds showing unexpected intersystem crossing (ISC) ability." Organic & Biomolecular Chemistry 16, no. 20 (2018): 3692–701. http://dx.doi.org/10.1039/c8ob00421h.

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26

Rigsby, Emily M., Tsumugi Miyashita, Dmitry A. Fishman, Sean T. Roberts, and Ming L. Tang. "CdSe nanocrystal sensitized photon upconverting film." RSC Advances 11, no. 49 (2021): 31042–46. http://dx.doi.org/10.1039/d1ra06562a.

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27

Ma, Jie, Xiaolin Yuan, Betül Küçüköz, Shengfu Li, Caishun Zhang, Poulomi Majumdar, Ahmet Karatay, et al. "Resonance energy transfer-enhanced rhodamine–styryl Bodipy dyad triplet photosensitizers." J. Mater. Chem. C 2, no. 20 (2014): 3900–3913. http://dx.doi.org/10.1039/c3tc32456g.

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28

Gray, Victor, Pan Xia, Zhiyuan Huang, Emily Moses, Alexander Fast, Dmitry A. Fishman, Valentine I. Vullev, Maria Abrahamsson, Kasper Moth-Poulsen, and Ming Lee Tang. "CdS/ZnS core–shell nanocrystal photosensitizers for visible to UV upconversion." Chemical Science 8, no. 8 (2017): 5488–96. http://dx.doi.org/10.1039/c7sc01610g.

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29

Abrahamse, Heidi, and Michael R. Hamblin. "New photosensitizers for photodynamic therapy." Biochemical Journal 473, no. 4 (February 9, 2016): 347–64. http://dx.doi.org/10.1042/bj20150942.

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Photodynamic therapy (PDT) was discovered more than 100 years ago, and has since become a well-studied therapy for cancer and various non-malignant diseases including infections. PDT uses photosensitizers (PSs, non-toxic dyes) that are activated by absorption of visible light to initially form the excited singlet state, followed by transition to the long-lived excited triplet state. This triplet state can undergo photochemical reactions in the presence of oxygen to form reactive oxygen species (including singlet oxygen) that can destroy cancer cells, pathogenic microbes and unwanted tissue. The dual-specificity of PDT relies on accumulation of the PS in diseased tissue and also on localized light delivery. Tetrapyrrole structures such as porphyrins, chlorins, bacteriochlorins and phthalocyanines with appropriate functionalization have been widely investigated in PDT, and several compounds have received clinical approval. Other molecular structures including the synthetic dyes classes as phenothiazinium, squaraine and BODIPY (boron-dipyrromethene), transition metal complexes, and natural products such as hypericin, riboflavin and curcumin have been investigated. Targeted PDT uses PSs conjugated to antibodies, peptides, proteins and other ligands with specific cellular receptors. Nanotechnology has made a significant contribution to PDT, giving rise to approaches such as nanoparticle delivery, fullerene-based PSs, titania photocatalysis, and the use of upconverting nanoparticles to increase light penetration into tissue. Future directions include photochemical internalization, genetically encoded protein PSs, theranostics, two-photon absorption PDT, and sonodynamic therapy using ultrasound.

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30

Ma, Lihua, Huimin Guo, Qiuting Li, Song Guo, and Jianzhang Zhao. "Visible light-harvesting cyclometalated Ir(iii) complexes as triplet photosensitizers for triplet–triplet annihilation based upconversion." Dalton Transactions 41, no. 35 (2012): 10680. http://dx.doi.org/10.1039/c2dt30955f.

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31

Qian, Mengdan, Weiying Hou, Dandan Chen, Xiaosong Li, Qidai Chen, and Changfeng Wu. "Metalloporphyrin loaded semiconducting polymer dots as potent photosensitizers via triplet-triplet energy transfer." Journal of Photochemistry and Photobiology A: Chemistry 383 (October 2019): 111988. http://dx.doi.org/10.1016/j.jphotochem.2019.111988.

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32

Mazzone, Gloria, Nino Russo, and Emilia Sicilia. "Theoretical investigation of the absorption spectra and singlet-triplet energy gap of positively charged tetraphenylporphyrins as potential photodynamic therapy photosensitizers." Canadian Journal of Chemistry 91, no. 9 (September 2013): 902–6. http://dx.doi.org/10.1139/cjc-2012-0449.

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DFT and TD-DFT calculations have been performed on a series of positively charged tetraphenylporphyrins with the aim to check whether these compounds can be used as photosensitizers in photodynamic therapy (PDT). Absorption spectra and singlet-triplet energy gaps have been computed by using the BP86, PBE0, and ωB97XD exchange-correlation functionals. Polarizable continuum model (PCM) has been used to take into account solvent effects. A careful analysis has been made on the Q-band, localized in the near-red visible region of the spectrum, since it plays a fundamental role in the drug design of new photodynamic therapy photosensitizers. Our results show that all the examined molecules have an adsorption band that falls in the so-called therapeutic window and possess a singlet-triplet energy gap able to promote the excitation of molecular oxygen from its ground triplet to the excited singlet state. The use of the ωB97XD exchange correlation functional, which accounts for dispersion interactions, allows calculating excitation energy values close to the experimental values.

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33

Mencaroni, Letizia, Benedetta Carlotti, Alessio Cesaretti, Fausto Elisei, Ana Grgičević, Irena Škorić, and Anna Spalletti. "Competition between fluorescence and triplet production ruled by nitro groups in one-arm and two-arm styrylbenzene heteroanalogues." Photochemical & Photobiological Sciences 19, no. 12 (2020): 1665–76. http://dx.doi.org/10.1039/d0pp00271b.

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One-arm nitro-stilbenoids shows high triplet yield, appealing for optoelectronic and photovoltaic devices while double-arm analogues, showing appreciable TPA, are candidates as emitting probes and traceable photosensitizers for photodynamic therapy.

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34

Teeuwen, Paula C. P., Zoi Melissari, Mathias O. Senge, and René M. Williams. "Metal Coordination Effects on the Photophysics of Dipyrrinato Photosensitizers." Molecules 27, no. 20 (October 17, 2022): 6967. http://dx.doi.org/10.3390/molecules27206967.

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Within this work, we review the metal coordination effect on the photophysics of metal dipyrrinato complexes. Dipyrrinato complexes are promising candidates in the search for alternative transition metal photosensitizers for application in photodynamic therapy (PDT). These complexes can be activated by irradiation with light of a specific wavelength, after which, cytotoxic reactive oxygen species (ROS) are generated. The metal coordination allows for the use of the heavy atom effect, which can enhance the triplet generation necessary for generation of ROS. Additionally, the flexibility of these complexes for metal ions, substitutions and ligands allows the possibility to tune their photophysical properties. A general overview of the mechanism of photodynamic therapy and the properties of the triplet photosensitizers is given, followed by further details of dipyrrinato complexes described in the literature that show relevance as photosensitizers for PDT. In particular, the photophysical properties of Re(I), Ru(II), Rh(III), Ir(III), Zn(II), Pd(II), Pt(II), Ni(II), Cu(II), Ga(III), In(III) and Al(III) dipyrrinato complexes are discussed. The potential for future development in the field of (dipyrrinato)metal complexes is addressed, and several new research topics are suggested throughout this work. We propose that significant advances could be made for heteroleptic bis(dipyrrinato)zinc(II) and homoleptic bis(dipyrrinato)palladium(II) complexes and their application as photosensitizers for PDT.

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35

Majumdar, Poulomi, Raju Nomula, and Jianzhang Zhao. "Activatable triplet photosensitizers: magic bullets for targeted photodynamic therapy." J. Mater. Chem. C 2, no. 30 (2014): 5982–97. http://dx.doi.org/10.1039/c4tc00659c.

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36

Zhao, Jianzhang, Wanhua Wu, Jifu Sun, and Song Guo. "ChemInform Abstract: Triplet Photosensitizers: From Molecular Design to Applications." ChemInform 44, no. 34 (August 1, 2013): no. http://dx.doi.org/10.1002/chin.201334236.

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37

Yi, Xiuyu, Jianzhang Zhao, Jifu Sun, Song Guo, and Hongli Zhang. "Visible light-absorbing rhenium(i) tricarbonyl complexes as triplet photosensitizers in photooxidation and triplet–triplet annihilation upconversion." Dalton Trans. 42, no. 6 (2013): 2062–74. http://dx.doi.org/10.1039/c2dt32420b.

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38

Alberto, Marta E., Bruna C. De Simone, Gloria Mazzone, Emilia Sicilia, and Nino Russo. "The heavy atom effect on Zn(ii) phthalocyanine derivatives: a theoretical exploration of the photophysical properties." Physical Chemistry Chemical Physics 17, no. 36 (2015): 23595–601. http://dx.doi.org/10.1039/c5cp03833b.

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Absorption electronic spectra, singlet–triplet energy gaps and spin–orbit matrix elements have been computed at DFT and TDDFT levels of theory for a series of substituted Zn(ii)-phthalocyanines (ZnPcs), recently proposed as potential photosensitizers in photodynamic therapy (PDT).

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39

Grusenmeyer, Tod A., Albert W. King, Joel T. Mague, Jeffrey J. Rack, and Russell H. Schmehl. "Sn(iv) Schiff base complexes: triplet photosensitizers for photoredox reactions." Dalton Trans. 43, no. 47 (2014): 17754–65. http://dx.doi.org/10.1039/c4dt01427h.

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40

Wu, Wanhua, Xiaoneng Cui, and Jianzhang Zhao. "Hetero Bodipy-dimers as heavy atom-free triplet photosensitizers showing a long-lived triplet excited state for triplet–triplet annihilation upconversion." Chemical Communications 49, no. 79 (2013): 9009. http://dx.doi.org/10.1039/c3cc45470c.

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41

Xiao, Yao, Xiaoyu Huang, Jiao Feng, Zhigang Ni, Lizhi Gai, Xuqiong Xiao, Xinbing Sui, and Hua Lu. "A simple route toward triplet-forming thionated BODIPY-based photosensitizers." Dyes and Pigments 200 (April 2022): 110167. http://dx.doi.org/10.1016/j.dyepig.2022.110167.

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42

Antunes, Edith M., and Tebello Nyokong. "Synthesis and Photophysical Properties of Tetra- and Octasubstituted Phosphorous Oxide Triazatetrabenzcorrole Photosensitizers." Metal-Based Drugs 2008 (March 3, 2008): 1–9. http://dx.doi.org/10.1155/2008/498916.

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The synthesis of phosphorous oxide triazatetrabenzcorroles (TBC) tetra- (9, 11) or octa- (13) substituted on the ring with halogenated functional groups is reported. The complexes are not aggregated in dimethylsulfoxide (DMSO) and show solubility in solvents such as pyridine. The Q band absorption spectra of the complexes are red-shifted compared to unsubstituted PTBC. The latter complex shows a large triplet lifetime (1.7 milliseconds), higher than for MPc derivatives. The chlorinated derivatives show good triplet yields (ΦT∼ 0.46 and 0.36) and relatively long lifetimes (256 and 452 microseconds), respectively, for 11 and 13.

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43

Wang, Zhijia, and Jianzhang Zhao. "Bodipy–Anthracene Dyads as Triplet Photosensitizers: Effect of Chromophore Orientation on Triplet-State Formation Efficiency and Application in Triplet–Triplet Annihilation Upconversion." Organic Letters 19, no. 17 (August 15, 2017): 4492–95. http://dx.doi.org/10.1021/acs.orglett.7b02047.

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44

Zhang, Caishun, Jianzhang Zhao, Shuo Wu, Zilong Wang, Wanhua Wu, Jie Ma, Song Guo, and Ling Huang. "Intramolecular RET Enhanced Visible Light-Absorbing Bodipy Organic Triplet Photosensitizers and Application in Photooxidation and Triplet–Triplet Annihilation Upconversion." Journal of the American Chemical Society 135, no. 28 (July 8, 2013): 10566–78. http://dx.doi.org/10.1021/ja405170j.

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45

Mabato, Beatrix Rosette Go, Yong Jie Li, Dan Dan Huang, Yalin Wang, and Chak K. Chan. "Comparison of aqueous secondary organic aerosol (aqSOA) product distributions from guaiacol oxidation by non-phenolic and phenolic methoxybenzaldehydes as photosensitizers in the absence and presence of ammonium nitrate." Atmospheric Chemistry and Physics 23, no. 4 (March 2, 2023): 2859–75. http://dx.doi.org/10.5194/acp-23-2859-2023.

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Abstract. Aromatic carbonyls (e.g., methoxybenzaldehydes), an important class of photosensitizers, are abundant in the atmosphere. Photosensitization and nitrate-mediated photo-oxidation can occur simultaneously, yet studies about their interactions, particularly for aqueous secondary organic aerosol (aqSOA) formation, remain limited. This study compared non-phenolic (3,4-dimethoxybenzaldehyde, DMB) and phenolic (vanillin, VL) methoxybenzaldehydes as photosensitizers for aqSOA formation via guaiacol (GUA) oxidation in the absence and presence of ammonium nitrate (AN) under atmospherically relevant cloud and fog conditions. GUA oxidation by triplet excited states of DMB (3DMB∗) (GUA + DMB) was ∼ 4 times faster and exhibited greater light absorption than oxidation by 3VL∗ (GUA + VL). Both GUA + DMB and GUA + VL formed aqSOA composed of oligomers, functionalized monomers, oxygenated ring-opening species, and N-containing products in the presence of AN. The observation of N-heterocycles such as imidazoles indicates the participation of ammonium in the reactions. The majority of generated aqSOA comprises potential brown carbon (BrC) chromophores. Oligomerization and functionalization dominated in GUA + DMB and GUA + VL, but functionalization appeared to be more important in GUA + VL due to contributions from VL itself. AN did not significantly affect the oxidation kinetics, but it had distinct effects on the product distributions, likely due to differences in the photosensitizing abilities and structural features of DMB and VL. In particular, the more extensive fragmentation in GUA + DMB than in GUA + VL likely generated more N-containing products in GUA + DMB + AN. In GUA + VL + AN, the increased oligomers may be due to VL-derived phenoxy radicals induced by ⚫OH or ⚫NO2 from nitrate photolysis. Furthermore, increased nitrated products observed in the presence of both DMB or VL and AN than in AN alone imply that photosensitized reactions may promote nitration. This work demonstrates how the structural features of photosensitizers affect aqSOA formation via non-carbonyl phenol oxidation. Potential interactions between photosensitization and AN photolysis were also elucidated. These findings facilitate a better understanding of photosensitized aqSOA formation and highlight the importance of AN photolysis in these reactions.

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Guo, Song, Wanhua Wu, Huimin Guo, and Jianzhang Zhao. "Room-Temperature Long-Lived Triplet Excited States of Naphthalenediimides and Their Applications as Organic Triplet Photosensitizers for Photooxidation and Triplet–Triplet Annihilation Upconversions." Journal of Organic Chemistry 77, no. 8 (April 2, 2012): 3933–43. http://dx.doi.org/10.1021/jo3003002.

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Guo, Song, Jifu Sun, Lihua Ma, Wenqin You, Pei Yang, and Jianzhang Zhao. "Visible light-harvesting naphthalenediimide (NDI)-C60 dyads as heavy-atom-free organic triplet photosensitizers for triplet–triplet annihilation based upconversion." Dyes and Pigments 96, no. 2 (February 2013): 449–58. http://dx.doi.org/10.1016/j.dyepig.2012.09.008.

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Huang, Dandan, Jianzhang Zhao, Wanhua Wu, Xiuyu Yi, Pei Yang, and Jie Ma. "Visible-Light-Harvesting Triphenylamine Ethynyl C60-BODIPY Dyads as Heavy-Atom-Free Organic Triplet Photosensitizers for Triplet-Triplet Annihilation Upconversion." Asian Journal of Organic Chemistry 1, no. 3 (September 17, 2012): 264–73. http://dx.doi.org/10.1002/ajoc.201200062.

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Korff, Marvin, Tiffany O. Paulisch, Frank Glorius, Nikos L. Doltsinis, and Bernhard Wünsch. "Photocatalytic Isomerization of (E)-Anethole to (Z)-Anethole." Molecules 27, no. 16 (August 22, 2022): 5342. http://dx.doi.org/10.3390/molecules27165342.

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Natural product (E)-anethole was isomerized to (Z)-anethole in a photocatalytic reaction. For this purpose, a self-designed cheap photoreactor was constructed. Among 11 photosensitizers (organo and metal complex compounds), Ir(p-tBu-ppy)3 led to the highest conversion. Triplet energies of (E)- and (Z)-anethole were predicted theoretically by DFT calculations to support the selection of appropriate photosensitizers. A catalyst loading of 0.1 mol% gave up to 90% conversion in gram scale. Further additives were not required and mild irradiation with light of 400 nm overnight was sufficient. As a proof of concept, (E)- and (Z)-anethole were dihydroxylated diastereoselectively to obtain diastereomerically pure like- and unlike-configured diols, respectively.

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Post, Alan J., and Harry Morrison. "Reactions of Oxaziridines Initiated by n,.pi.* Triplet States of Photosensitizers." Journal of the American Chemical Society 117, no. 29 (July 1995): 7812–13. http://dx.doi.org/10.1021/ja00134a029.

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