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Journal articles on the topic 'Heteroacenes'

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Published: 11 March 2023

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1

Bunz, Uwe H. F. "N-Heteroacenes." Chemistry - A European Journal 15, no. 28 (July 13, 2009): 6780–89. http://dx.doi.org/10.1002/chem.200900990.

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2

Bunz, Uwe H. F. "The larger N-heteroacenes." Pure and Applied Chemistry 82, no. 4 (March 20, 2010): 953–68. http://dx.doi.org/10.1351/pac-con-09-09-17.

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The history and development of pyrazine- and pyridine-type heteroacenes and their use in solid-state organic electronics are discussed and reviewed. The larger N-heteroacenes are potential electron- or hole-transporting materials and should therefore complement acenes in organic electronics. As they feature electronegative nitrogen ring atoms in their molecular skeleton, issues with oxidation should be less problematic when comparing them to the larger acenes such as pentacene. This paper covers the synthesis and the solid-state packing of larger (tetracene/pentacene-based) N,N-heterocylic acenes as well as the question of the interplay of aromaticity and antiaromaticity in the known larger N-heteroacenes and their N,N-dihydro-derivatives; also illuminated are their optical properties. A literature overview is provided. Keywords: acenes; alkynes; heterocycles; organic chemistry; organic electronics.
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3

Lepeltier, Marc, Olena Lukoyanova, Alex Jacobson, Shehzad Jeeva, and Dmitrii F. Perepichka. "New azaborine-thiophene heteroacenes." Chemical Communications 46, no. 37 (2010): 7007. http://dx.doi.org/10.1039/c0cc01963a.

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4

Ding, Fangwei, Debin Xia, Congwu Ge, Zhenchao Kang, Yulin Yang, Ruiqing Fan, Kaifeng Lin, and Xike Gao. "Indenone-fused N-heteroacenes." Journal of Materials Chemistry C 7, no. 45 (2019): 14314–19. http://dx.doi.org/10.1039/c9tc04962b.

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5

Feofanov, Mikhail, Vladimir Akhmetov, Ryo Takayama, and Konstantin Amsharov. "Transition-metal free synthesis of N-aryl carbazoles and their extended analogs." Organic & Biomolecular Chemistry 19, no. 33 (2021): 7172–75. http://dx.doi.org/10.1039/d1ob00940k.

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6

Zhang, Yubao, Jiulin Shi, Xingdao He, and Guoli Tu. "All-thiophene-substituted N-heteroacene electron-donor materials for efficient organic solar cells." Journal of Materials Chemistry A 4, no. 35 (2016): 13519–24. http://dx.doi.org/10.1039/c6ta03784d.

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7

Zhang, Wanzheng, Yubin Fu, Peirong Qiang, Jens Hunger, Shuai Bi, Wenbei Zhang, and Fan Zhang. "syn-BN-heteroacene cored conjugated oligomers with finely tuned blue-violet luminescent properties." Organic & Biomolecular Chemistry 15, no. 34 (2017): 7106–11. http://dx.doi.org/10.1039/c7ob01679d.

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8

Bulumulla, Chandima, Ruwan Gunawardhana, Sang Ha Yoo, Cody R. Mills, Ruvanthi N. Kularatne, Thomas N. Jackson, Michael C. Biewer, Enrique D. Gomez, and Mihaela C. Stefan. "The effect of single atom replacement on organic thin film transistors: case of thieno[3,2-b]pyrrole vs. furo[3,2-b]pyrrole." Journal of Materials Chemistry C 6, no. 37 (2018): 10050–58. http://dx.doi.org/10.1039/c8tc02887g.

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9

Bunz, Uwe H. F. "The Larger Linear N-Heteroacenes." Accounts of Chemical Research 48, no. 6 (May 13, 2015): 1676–86. http://dx.doi.org/10.1021/acs.accounts.5b00118.

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10

Ding, Fangwei, Debin Xia, Weipeng Sun, Wei Chen, Yulin Yang, Kaifeng Lin, Feibao Zhang, and Xugang Guo. "Sulfur‐Containing Bent N‐Heteroacenes." Chemistry – A European Journal 25, no. 66 (October 31, 2019): 15106–11. http://dx.doi.org/10.1002/chem.201902984.

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11

Gong, Peng, Kaiqi Ye, Jingbo Sun, Peng Chen, Pengchong Xue, Hao Yang, and Ran Lu. "Electroluminescence and fluorescence response towards acid vapors depending on the structures of indole-fused phospholes." RSC Advances 5, no. 115 (2015): 94990–96. http://dx.doi.org/10.1039/c5ra19867d.

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12

Matsuda, Takanori, and Hirotaka Ito. "Synthesis of indole-fused heteroacenes by cascade cyclisation involving rhodium(ii)-catalysed intramolecular C–H amination." Organic & Biomolecular Chemistry 16, no. 36 (2018): 6703–7. http://dx.doi.org/10.1039/c8ob01837e.

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13

Wu, Di, Jueting Zheng, Chenyong Xu, Dawei Kang, Wenjing Hong, Zheng Duan, and François Mathey. "Phosphindole fused pyrrolo[3,2-b]pyrroles: a new single-molecule junction for charge transport." Dalton Transactions 48, no. 19 (2019): 6347–52. http://dx.doi.org/10.1039/c9dt01299k.

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A new family of phosphindole fused ladder-type heteroacenes with a pyrrolo[3,2-b]pyrrole core were synthesized and characterized, which show good luminescence efficiency, high thermostability and tunable conductance.
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14

Cheng, Na, Feng Chen, Colm Durkan, Nan Wang, Yuanyuan He, and Jianwei Zhao. "Electron transport behavior of quinoidal heteroacene-based junctions: effective electron-transport pathways and quantum interference." Physical Chemistry Chemical Physics 20, no. 45 (2018): 28860–70. http://dx.doi.org/10.1039/c8cp05901b.

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Due to the additional p-electrons of the S/O atom, the electron transport behavior of heteroacenes is regulated through quantum interference, showing a significant diversity of the current–voltage curves.
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15

Qu, Hemi, and Chunyan Chi. "Synthetic Chemistry of Acenes and Heteroacenes." Current Organic Chemistry 14, no. 18 (November 1, 2010): 2070–108. http://dx.doi.org/10.2174/138527210793351580.

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16

Hu, Ben-Lin, Cunbin An, Manfred Wagner, Georgia Ivanova, Anela Ivanova, and Martin Baumgarten. "Three-Dimensional Pyrene-Fused N-Heteroacenes." Journal of the American Chemical Society 141, no. 13 (March 12, 2019): 5130–34. http://dx.doi.org/10.1021/jacs.9b01082.

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17

Müllen, K., P. Gao, D. Beckmann, H. Tsao, X. Feng, V. Enkelmann, M. Baumgarten, and W. Pisula. "Heteroacenes for Organic Field-Effect Transistors." Synfacts 2009, no. 03 (February 19, 2009): 0265. http://dx.doi.org/10.1055/s-0028-1087765.

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18

Laughlin, Feng Li, Nihal Deligonul, Arnold L. Rheingold, James A. Golen, Brynna J. Laughlin, Rhett C. Smith, and John D. Protasiewicz. "Fluorescent Heteroacenes with Multiply-Bonded Phosphorus." Organometallics 32, no. 23 (November 15, 2013): 7116–21. http://dx.doi.org/10.1021/om400838g.

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19

Lepeltier, Marc, Olena Lukoyanova, Alex Jacobson, Shehzad Jeeva, and Dmitrii F. Perepichka. "ChemInform Abstract: New Azaborine-Thiophene Heteroacenes." ChemInform 42, no. 4 (December 30, 2010): no. http://dx.doi.org/10.1002/chin.201104188.

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20

Bunz, Uwe H. F. "ChemInform Abstract: The Larger N-Heteroacenes." ChemInform 41, no. 39 (September 2, 2010): no. http://dx.doi.org/10.1002/chin.201039245.

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21

Bunz, Uwe H. F., and Jens U. Engelhart. "The Palladium Way to N-Heteroacenes." Chemistry - A European Journal 22, no. 14 (February 17, 2016): 4680–89. http://dx.doi.org/10.1002/chem.201505018.

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22

Yamaguchi, Shigehiro, Caihong Xu, and Toshihiro Okamoto. "Ladder π-conjugated materials with main group elements." Pure and Applied Chemistry 78, no. 4 (January 1, 2006): 721–30. http://dx.doi.org/10.1351/pac200678040721.

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Ladder-type π-conjugated skeletons are promising building units for new materials for organic electronics, wherein their annelated coplanar structures enhance the π-conjugation, leading to a set of desirable properties such as intense fluorescence and high carrier mobility. As a new entry into this class of skeletons, we now disclose two series of ladder molecules, i.e., silicon- and carbon-bridged oligo(p-phenylenevinylene)s and thiophene- and selenophene-based heteroacenes. The former ladder molecules contain the silole substructure in which the silicon bridges affect the electronic structure and thus photophysical properties through the σ*-π* conjugation. The latter heteroacenes can be recognized as the heteroatom analogs of acenes and may be promising materials for organic thin film transistors. These two series of molecules have been synthesized based on newly developed intramolecular cyclizations of acetylenic compounds.
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23

Shan, Xiang-Huan, Bo Yang, Jian-Ping Qu, and Yan-Biao Kang. "CuSO4-Catalyzed dual annulation to synthesize O, S or N-containing tetracyclic heteroacenes." Chemical Communications 56, no. 29 (2020): 4063–66. http://dx.doi.org/10.1039/d0cc01172j.

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In this work, CuSO4 is utilized as a practical redox catalyst for tandem dual annulation in the synthesis of indole-fused tetracyclic heteroacenes, which are important skeletons in both medicinal chemistry and materials chemistry.
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24

Wu, Yimin, Wei Li, Linfeng Jiang, Luoqiang Zhang, Jingbo Lan, and Jingsong You. "Rhodium-catalyzed ortho-heteroarylation of phenols: directing group-enabled switching of the electronic bias for heteroaromatic coupling partner." Chemical Science 9, no. 33 (2018): 6878–82. http://dx.doi.org/10.1039/c8sc02529k.

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A highly efficient ortho-heteroarylation of phenols with diverse electron-rich heteroarenes has been developed to forge heteroaryl-2-hydroxyphenyl structural motifs. The removal of the directing group and subsequent intramolecular cyclization make this protocol applicable in the rapid construction of π-conjugated heteroacenes.
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25

Müller, Matthias, Lukas Ahrens, Victor Brosius, Jan Freudenberg, and Uwe H. F. Bunz. "Unusual stabilization of larger acenes and heteroacenes." Journal of Materials Chemistry C 7, no. 45 (2019): 14011–34. http://dx.doi.org/10.1039/c9tc04843j.

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26

Brier, Eduard, Christoph Wetzel, Michael Bauer, Elena Mena-Osteritz, Markus Wunderlin, and Peter Bäuerle. "S,N-Heteroacenes Up to a Tridecamer." Chemistry of Materials 31, no. 17 (June 20, 2019): 7007–23. http://dx.doi.org/10.1021/acs.chemmater.9b01652.

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27

Anthony, John E. "Functionalized Acenes and Heteroacenes for Organic Electronics." Chemical Reviews 106, no. 12 (December 2006): 5028–48. http://dx.doi.org/10.1021/cr050966z.

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28

Nagahora, Noriyoshi, Tomoko Kushida, Kosei Shioji, and Kentaro Okuma. "Dicationic Heteroacenes Containing Thio- or Selenopyrylium Moieties." Organometallics 38, no. 8 (April 11, 2019): 1800–1808. http://dx.doi.org/10.1021/acs.organomet.9b00100.

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29

Bunz, Uwe H. F. "ChemInform Abstract: The Larger Linear N-Heteroacenes." ChemInform 46, no. 35 (August 13, 2015): no. http://dx.doi.org/10.1002/chin.201535264.

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30

Mishra, Amaresh. "Material perceptions and advances in molecular heteroacenes for organic solar cells." Energy & Environmental Science 13, no. 12 (2020): 4738–93. http://dx.doi.org/10.1039/d0ee02461a.

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31

Li, Guijie, Shaolin Zhou, Guowei Su, Yuanhong Liu, and Peng George Wang. "Improved Synthesis of Aryl-Substituted Anthracenes and Heteroacenes." Journal of Organic Chemistry 72, no. 25 (December 2007): 9830–33. http://dx.doi.org/10.1021/jo7017334.

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32

Wang, Xinyang, Fan Zhang, Jun Liu, Ruizhi Tang, Yubin Fu, Dongqing Wu, Qing Xu, Xiaodong Zhuang, Gufeng He, and Xinliang Feng. "Ladder-Type BN-Embedded Heteroacenes with Blue Emission." Organic Letters 15, no. 22 (October 24, 2013): 5714–17. http://dx.doi.org/10.1021/ol402745r.

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33

Hupf, Emanuel, Yuki Tsuchiya, Wayne Moffat, Letian Xu, Masato Hirai, Yuqiao Zhou, Michael J. Ferguson, et al. "A Modular Approach to Phosphorescent π-Extended Heteroacenes." Inorganic Chemistry 58, no. 19 (September 10, 2019): 13323–36. http://dx.doi.org/10.1021/acs.inorgchem.9b02213.

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34

Okamoto, Toshihiro, Kenichi Kudoh, Atsushi Wakamiya, and Shigehiro Yamaguchi. "General Synthesis of Thiophene and Selenophene-Based Heteroacenes." Organic Letters 7, no. 23 (November 2005): 5301–4. http://dx.doi.org/10.1021/ol0523650.

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35

Xu, Wan, Mengjie Wang, Zhiying Ma, Zhen Shan, Chunli Li, and Hua Wang. "Selenophene-Based Heteroacenes: Synthesis, Structures, and Physicochemical Behaviors." Journal of Organic Chemistry 83, no. 19 (September 2, 2018): 12154–63. http://dx.doi.org/10.1021/acs.joc.8b02107.

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36

Hu, Ben-Lin, Ke Zhang, Cunbin An, Dieter Schollmeyer, Wojciech Pisula, and Martin Baumgarten. "Layered Thiadiazoloquinoxaline-Containing Long Pyrene-Fused N-Heteroacenes." Angewandte Chemie 130, no. 38 (August 27, 2018): 12555–59. http://dx.doi.org/10.1002/ange.201803230.

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37

Qu, Hemi, and Chunyan Chi. "ChemInform Abstract: Synthetic Chemistry of Acenes and Heteroacenes." ChemInform 42, no. 14 (March 14, 2011): no. http://dx.doi.org/10.1002/chin.201114237.

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38

Gu, Xiao, Bowen Shan, Zikai He, and Qian Miao. "N-Phenylated N-Heteroacenes: Synthesis, Structures, and Properties." ChemPlusChem 82, no. 7 (October 11, 2016): 1034–38. http://dx.doi.org/10.1002/cplu.201600465.

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39

Hu, Ben-Lin, Ke Zhang, Cunbin An, Dieter Schollmeyer, Wojciech Pisula, and Martin Baumgarten. "Layered Thiadiazoloquinoxaline-Containing Long Pyrene-Fused N-Heteroacenes." Angewandte Chemie International Edition 57, no. 38 (August 27, 2018): 12375–79. http://dx.doi.org/10.1002/anie.201803230.

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40

Campbell, Josh, and Graeme Day. "Structure prediction of N-heteroacenes as potential organic semiconductors." Acta Crystallographica Section A Foundations and Advances 70, a1 (August 5, 2014): C1621. http://dx.doi.org/10.1107/s2053273314083788.

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Organic electronics offer exciting new alternatives to traditional inorganic devices based on advantages such as lower cost, ease of manufacture and flexibility. Small molecule semiconductors such as pentacene and rubrene are the focus of intense research due to performance approaching that of inorganic semiconductors. Charge transfer in polyaromatic hydrocarbons (PAHs) relies on the degree of π-conjugation and overlap of the π-systems of neighbouring molecules in the solid state. Small changes in the intermolecular interactions can lead to important changes in crystal packing and electronic properties. Thus, functionalization of PAHs is often used to improve their packing in the solid state. The addition of electronegative atoms into the ring system of pentacene has been proposed for improving stability while retaining attractive properties. [1] N-heteroacenes result from the substitution of nitrogen into the arene ring structure. The resulting potential for weak hydrogen bonding could direct coplanar molecular arrangements, sheet formation and favourable π-overlap for charge transport. Theoretical studies [2] have been carried out showing promising properties at the molecular level. As of yet no analysis of the solid state of these molecules has been performed to investigate how this substitution affects the packing and electronic properties. Here, we present the results of crystal structure prediction studies and calculation of charge transport properties aimed at understanding the influence of nitrogen substitution on the crystal packing of N-heteropentacenes and their performance as semiconducting materials.
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41

Santhini, P. V., Akhil Krishnan R, Sheba Ann Babu, Betna Shamlin Simethy, Gourab Das, Vakayil K. Praveen, Sunil Varughese, and Jubi John. "One-Pot MCR-Oxidation Approach toward Indole-Fused Heteroacenes." Journal of Organic Chemistry 82, no. 19 (September 25, 2017): 10537–48. http://dx.doi.org/10.1021/acs.joc.7b02039.

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42

Bunz, Uwe H. F., and Jan Freudenberg. "N-Heteroacenes and N-Heteroarenes as N-Nanocarbon Segments." Accounts of Chemical Research 52, no. 6 (June 6, 2019): 1575–87. http://dx.doi.org/10.1021/acs.accounts.9b00160.

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43

Bunz, Uwe H. F., Jens U. Engelhart, Benjamin D. Lindner, and Manuel Schaffroth. "Large N-Heteroacenes: New Tricks for Very Old Dogs?" Angewandte Chemie International Edition 52, no. 14 (February 18, 2013): 3810–21. http://dx.doi.org/10.1002/anie.201209479.

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44

Yang, Shuaijun, Bowen Shan, Xiaomin Xu, and Qian Miao. "Extension of N-Heteroacenes through a Four-Membered Ring." Chemistry - A European Journal 22, no. 19 (March 30, 2016): 6637–42. http://dx.doi.org/10.1002/chem.201600918.

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45

Balaji, Ganapathy, Andrea M. Della Pelle, Bhooshan C. Popere, A. Chandrasekaran, and S. Thayumanavan. "Synthesis and properties of thienopyrrole based heteroacenes – indolodibenzothienopyrrole and dicarbazolodithienopyrrole." Organic & Biomolecular Chemistry 10, no. 17 (2012): 3455. http://dx.doi.org/10.1039/c2ob25087j.

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46

Verbitskiy, Egor V., Ekaterina M. Cheprakova, Nadezhda I. Makarova, Igor V. Dorogan, Anatoly V. Metelitsa, Vladimir I. Minkin, Pavel A. Slepukhin, et al. "Heteroacenes Bearing the Pyrimidine Scaffold: Synthesis, Photophysical and Electrochemical Properties." European Journal of Organic Chemistry 2016, no. 7 (February 8, 2016): 1420–28. http://dx.doi.org/10.1002/ejoc.201501450.

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47

HE, Yuan-Hang, Ren-Jie HUI, Yuan-Ping YI, and Zhi-Gang SHUAI. "Theoretically Rational Designs of Transport Organic Semiconductors Based on Heteroacenes." Chinese Journal of Chemistry 26, no. 6 (June 2008): 1005–10. http://dx.doi.org/10.1002/cjoc.200890179.

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48

Meng, Linghao, Debin Xia, Shihui Liu, Xiaoqing Yi, Fangwei Ding, Ruiqing Fan, and Yulin Yang. "Dimesitylboron Endcapped S,N-Heteroacenes: Syntheses, Photophysical and Fluoride-binding Properties." Chemistry Letters 49, no. 8 (August 5, 2020): 947–51. http://dx.doi.org/10.1246/cl.200290.

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49

Wetzel, Christoph, Amaresh Mishra, Elena Mena-Osteritz, Andreas Liess, Matthias Stolte, Frank Würthner, and Peter Bäuerle. "Synthesis and Structural Analysis of Thiophene-Pyrrole-Based S,N-Heteroacenes." Organic Letters 16, no. 2 (December 20, 2013): 362–65. http://dx.doi.org/10.1021/ol403153z.

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50

Zhang, You-Dan, Yishi Wu, Yanqing Xu, Qiang Wang, Ke Liu, Jian-Wei Chen, Jing-Jing Cao, Chunfeng Zhang, Hongbing Fu, and Hao-Li Zhang. "Excessive Exoergicity Reduces Singlet Exciton Fission Efficiency of Heteroacenes in Solutions." Journal of the American Chemical Society 138, no. 21 (May 19, 2016): 6739–45. http://dx.doi.org/10.1021/jacs.6b03829.

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