Dissertations / Theses on the topic 'Fluorofori'

Le micelle hanno un utilizzo sempre più vasto nel campo del drug delivery grazie alle loro caratteristiche che le rende capaci di inglobare principi farmacologici all'interno del nucleo idrofobico e trasportarli all'interno delle cellule. Lo scopo del lavoro di tesi si è diviso in tre macro-obiettivi. Il primo riguarda la messa a punto e perfezionamento di una via di sintesi ottimale per l’ottenimento di un copolimero a blocchi con caratteristiche anfifiliche. Il secondo riguarda la messa a punto e la realizzazione di reazioni di post-funzionalizzazione di questo copolimero anfifilico con gruppi cromoforici al fine di ottenere macromolecole marcate e tracciabili tramite metodi fluorimetrici. L'obiettivo finale è quello di ottenere delle micelle polimeriche utilizzando i copolimeri anfifilici precedentemente sintetizzati. I copolimeri a blocchi sono stati ottenuti polimerizzando il glicidil metacrilato tramite tecnica RAFT e successivamente utilizzando il poli(glicidil metacrilato) come agente macroRAFT per la copolimerizzazione del butil metacrilato. Il copolimero a blocchi poli(glicidil metacrilato)-poli(butil metacrilato) è stato reso anfifilico tramite funzionalizzazione con morfolina (ammina secondaria). il poli(2-idrossi-3-morfolinopropil metacrilato)-b-poli(butil metacrilato) è stato funzionalizzato utilizzando 4-cloro-7-nitrobenzofurazano e rodamina B isotiocianato e queste reazioni hanno permesso di ottenere copolimeri con catene fluorescenti. Tutti i copolimeri anfifilici ottenuti sono stati utilizzati per ottenere gli aggregati micellari che hanno mostrato proprietà estremamente interessanti per un futuro utilizzo nel campo del drug delivery.

L’activació i funcionalització d’enllaços carboni-halogen poc reactius és un dels principals objectius de la química moderna. Els tres projectes d’investigació recollits en aquesta Tesi doctoral es centren en el desenvolupament de noves reaccions d’activació i trencament d’enllaços C-I, C-Br, C-Cl i C-F inerts. En el capítol 1 es descriu una nova transformació química, la síntesis catalitzada per Pd d’aroil acides a partir de iodoarens, CO i NaN3. Aquest procés catalític mostra una excel•lent eficiència (0.2% Pd) a més d’una excel•lent tolerància amb diferents grups funcionals. L’estudi del mecanisme de la reacció de acidocarbonilació ha permès demostrar l’existència de dos camins de reacció que tenen lloc en presencia de CO en excés i sota condicions de deficiència de CO. Els intermedis organometàl•lics implicats en el cicle catalític han estat aïllats i caracteritzats totalment, mitjançant diverses tècniques incloent difracció per raig X. El capítol 2 recull l’estudi del mecanisme de l’activació de Ph-X (X = I, Br, Cl) mitjançant complexes d’hidrur de Ru(II) utilitzant condicions extremadament suaus. Addicionalment, s’ha pogut demostrar que l’ordre zero observat en els estudis cinètics per a la reacció de [(Ph3P)4Ru(H)2] amb PhX (X = I, Br) troba el seu origen en un procés d’autocatàlisis poc evident. El capítol 3 es centra en la activació C-F del fortament inert fluoroform (CHF3), un gas subproducte industrial causant de l’efecte hivernacle, amb hidròxids i alcòxids de metalls alcalins. La reacció de MOR amb CHF3 condueix a la formació de ortoformiats, incloent l’exòtic en HC(OBu-t)3 amb excel•lents rendiments. Els resultats de la tesis han contribuït al desenvolupament de una nova metodologia, l’estudi de nous mecanismes de reacció i al desenvolupament de potencials solucions ecològiques.
La activación y funcionalización de enlaces carbono-halógeno no reactivos es uno de los principales desafíos en la química moderna. Los tres proyectos de investigación que se abordan en esta Tesis Doctoral tratan sobre el desarrollo de nuevas reacciones de activación y rotura de enlaces no activados como C-I, C-Br, C-Cl y C-F. El capítulo 1 describe una nueva transformación, la síntesis de aroil azidas a partir de iodoarenos, CO y NaN3 catalizada por paladio. Este proceso catalítico muestra una alta eficiencia (0.2% Pd) y una excelente tolerancia a distintos grupos funcionales. La detallada investigación mecanística de la reacción de azidocarbonilación reveló la presencia de dos diferentes vías que operan en presencia de un exceso o defecto de CO. Los intermedios organometálicos implicados en el ciclo catalítico han sido aislados y completamente caracterizados, incluyendo difracción de rayos X. El capítulo 2 detalla un estudio mecanístico de la activación de Ph-X (X = I, Br, Cl) con complejos de hidruro de Ru(II) en condiciones extremadamente suaves. El inusual orden cero cinético de la reacción de [(Ph3P)4Ru(H)2] con PhX (X = I, Br) se origina debido a una autocatálisis que ha sido reconocida y completamente demostrada. El capítulo 3 describe la activación de los enlaces C-F altamente inertes del fluoroformo (CHF3), un gas de efecto invernadero producido industrialmente, con hidróxidos y alcóxidos de metales alcalinos. La reaciión de MOR con CHF3 se ha demostrado para dar lugar a los correspondientes ortoformiatos, incluído el exótico HC(OBu-t)3, en rendimientos excelentes. Los resultados de la Tesis Doctoral contribuyen al desarrollo de nuevas metodologías, al conocimiento básico de mecanismo de reacción y a posibles soluciones ecológicas.
Activation and functionalization of unreactive carbon-halogen bonds is one of the primary tasks of modern chemistry. All three research projects fulfilled in the current Thesis deal with new reactions involving activation and cleavage of highly inert C-I, C-Br, C-Cl, and C-F bonds. Chapter 1 describes a new chemical transformation, Pd-catalyzed synthesis of aroyl azides from iodoarenes, CO, and NaN3. This catalytic process exhibits high efficiency (0.2% Pd) and excellent functional group tolerance. A detailed mechanistic study of the azidocarbonylation reaction has revealed two different reaction pathways operating in the presence of CO in excess and under CO-deficient conditions. Organometallic intermediates involved in the catalytic cycle have been isolated and fully characterized, including by X-ray diffraction. Chapter 2 reports a mechanistic study of the novel Ph-X (X = I, Br, Cl) activation with Ru(II) hydrido complexes under exceedingly mild conditions. Striking zeroth-order kinetics observed for the reaction of [(Ph3P)4Ru(H)2] with PhX (X = I, Br) originates from hidden autocatalysis that has been recognized and fully proven. Chapter 3 deals with C-F activation of highly inert fluoroform (CHF3), an industrially side-produced potent greenhouse gas, with alkali metal hydroxides and alkoxides. The reaction of MOR with CHF3 has been shown to furnish the corresponding orthoformates, exotic HC(OBu-t)3 included, in good to excellent yield. Results of the Thesis contribute to new methodology development, basic knowledge of reaction mechanisms, and potential ecological solutions.

Le trifluoromethane (ou fluoroforme) peut etre utilise comme source d'anion trifluoromethyle en presence de bases telles que t-buok (1,1eq. ) ou le couple n(sime#3)#3(1,5eq. )/f#-(1,5 ou 0,2eq. ) qui permet d'engendrer lentement le bis-(trimethylsilyl)amidure, in situ. Le dmf doit generalement etre present dans le milieu, voire employe comme solvant de la reaction ; son role est de stabiliser l'anion #-cf#3 sous la forme d'un gem-amino alcoolate (me#2n)ch(cf#3)o#-. Ce reactif devient alors l'espece trifluoromethylante reelle. Neanmoins, le systeme n(sime#3)#3/f#- rend possible la trifluoromethylation dans le thf du fait qu'il permet de maintenir une faible concentration en anion #-cf#3 qui peut ainsi etre directement piege par l'electrophile en presence. Appliquees aux disulfures ou aux diseleniures, les differentes methodes mises au point ont permis d'acceder aux trifluoromethyl sulfures ou seleniures, avec de bons rendements (54-82%). Les thio- ou selenocyanates peuvent egalement etre utilises comme precurseurs des rycf#3 (y = s ou se), cependant les resultats sont, dans ce cas, plus faibles (12-48%). De la meme facon, il est possible de preparer des alcools trifluoromethyles a partir des cetones non enolisables correspondantes (52-100%). Le fluorure et le dmf peuvent alors etre utilises en quantite catalytique : la reaction est menee dans le thf. Malgre sa forte basicite, le systeme n(sime#3)#3 (1,5eq. )/me#4nf (1,5eq. )/hcf#3 permet de trifluoromethyler des cetones enolisables avec des rendements faibles a moyens (26-45%). Enfin, nous avons mis en evidence que les alcools allyliques ou cyclohexadieniques -trifluoromethyles peuvent subir des substitutions nucleophiles de type sn#2 ou sn#1, pour conduire a des derives vinyliques, indeniques ou aromatiques trifluoromethyles fonctionnalises.

Le fluoroforme, encore tres peu exploite en synthese organique, s'avere etre un bon agent trifluoromethylant. Sa deprotonation a basse temperature dans le dmf genere un aminoalcoolate trifluoromethyle provenant de l'addition de l'anion cf 3 sur le groupement carbonyle du dmf. Cet intermediaire tetraedrique constitue une forme stable de l'anion cf 3 , sujet a l'-elimination dans la plupart des milieux, quelle que soit la temperature. Un aldehyde oppose a cet aminoalcoolate conduit par retour a temperature ambiante a l'alcool trifluoromethyle correspondant. Il est possible de transmetaller cet intermediaire a l'aide de sels de cuivre(i). L'aminoalcoolate cuivreux ainsi obtenu est alors stable a temperature ambiante pendant plusieurs heures et des etudes conduites par r. M. N. Du 1 9fluor montrent qu'en presence d'une base de lewis appropriee, il se transforme progressivement en trifluoromethylcuivreux, cf 3cu. Chauffe en presence d'un iodure aromatique, cet aminoalcoolate conduit a l',,-trifluorotoluene correspondant.

Identifying the cause of a disease and the mechanism responsible for dysfunction in our organism is crucial for determination of an effective treatment pathway. The most primary changes are these at the cellular level. Fluorescent sensors enable us to get insight into a world of biological structures and to study cellular processes essential for proper functioning of our organism. Therefore, this group of compounds has gained considerable attention over the past years as safe tools useful for diagnostics and searching for new therapeutic targets. The main goal of the PhD thesis was synthesis of new fluorophores based on a styrylquinoline scaffold and analysis of their properties. A big part of the research was biological tests which enabled to determine the application potential of the newly synthesized compounds as cellular dyes. The scope of work covered, among others, determination of characteristics of the compounds based on analysis of spectroscopic measurements. Additionally, to gain deeper understanding of spectroscopic nature of the dyes and to explain newly discovered relationships, theoretical calculations was carried out with use of Gaussian09 software and density functional theory (DFT). Moreover, biological experiments were performed to determine cytotoxicity of the compounds towards human colon cancer cell line HCT 116 and normal human dermal fibroblasts (NHDF). The place of dyes accumulation in a cell was determine as well. In the case of the lysosomal dye, the reason of significant change of emitted signal in acidic structures was also explained. Furthermore, an attempt was made to establish the mechanism of zinc ions binding to one of the compounds and to determine processes responsible for activation of the fluorescent response after chelation (CHEF, chelation - enhanced fluorescence). It is worth mentioning that good spectroscopic properties of obtained compounds and successfully performed cellular imaging experiments indicate their commercial potential.

Els compostos que incorporen un grup –CF3, especialment en anells aromàtics, són compostos àmpliament demandats com building blocks a la indústria agroquímica, farmacèutica i de materials. Mentre que s’ha fet un progrés considerable amb les trifluorometilacions aromàtiques catalitzades per coure, sorprenentment hi ha poca recerca de cara a entendre els mecanismes d’aquesta reacció. En aquesta Tesi es desenvolupen per primer cop, de manera combinada, estudis experimentals i computacionals que tenen per objectiu específic l’elucidació del mecanisme de trifluorometilació d’haloarens. El CuCF3 utilitzat a l’estudi va ser preparat d’acord a la reacció de cupració directa de fluoroform, recentment descoberta pel nostre grup. Per aquesta important transformació sense precedents, vam dur a terme estudis detallats del seu mecanisme, descrit en el Capítol 1. Es va concloure que el contraió K+ té un rol crucial a la formació de l’enllaç Cu-CF3. L’addició d’un lligand amb gran afinitat pel K+ resulta en una inhibició significant del procés de cupració. El Capítol 2 descriu una àmplia investigació sobre el mecanisme de trifluorometilació d’halurs d’aril, que revela un mecanisme no-radicalari, implicant una addició oxidativa Ar-Hal al centre Cu(I), essent l’etapa determinant de la velocitat de reacció. El Capítol 3 tracta sobre l’efecte accelerador del substituent en orto a les reaccions d’acoblament catalitzades per Cu, efecte ja conegut des de fa temps però no explicat. Amb contribucions menors a nivell electrònic, aquest efecte ve determinat per la coordinació estabilitzant del substituent en orto al Cu durant l’estat de transició i per la càrrega estèrica, que augmenten l’estat energètic de l’haloarè. El Capítol 4 descriu els estudis teòrics sobre les propietats electròniques del grup -CF3 a la química orgànica i organometàl•lica. Evidentment, aquest tema és molt important per entendre els mecanismes de reacció i pel desenvolupament de la investigació de reaccions de trifluorometilació catalitzades per metalls.
Los compuestos que incorporan un grupo –CF3, especialmente en anillos aromáticos, son compuestos con gran demanda como building blocks para la industria agroquímica, farmacéutica y de materiales. Mientras que se ha progresado considerablemente con las trifluorometilaciones aromáticas catalizadas por cobre, sorprendentemente hay poca investigación referente a entender los mecanismos de esta reacción. En esta Tesis se desarrollan por primera vez, de manera combinada, estudios experimentales y computacionales que tienen por objetivo la determinación del mecanismo de trifluorometilación de hallaremos. El CuCF3 utilizado fue preparado de acuerdo a la reacción de cupración directa de fluoroformo, recientemente descubierta por nuestro grupo. Debido a esta importante transformación sin precedentes, se hicieron estudios de su mecanismo, descritos en el Capítulo 1. Se concluyó que el catión K+ tiene un rol crucial para la formación del enlace Cu-CF3. La adición de un ligando con gran afinidad por el K+ resultó en una inhibición significativa del proceso de cupración. El Capítulo 2 describe una amplia investigación sobre el mecanismo de trifluorometilación de haluros de arilo, que revela un mecanismo no-radicalario, implicando una adición oxidativa Ar-Hal al centro Cu(I), siendo la etapa determinante de la velocidad de reacción. El Capítulo 3 trata sobre el efecto acelerador del sustituyente en orto en las reacciones de acoplamiento mediadas por Cu, efecto ya conocido pero inexplicado. Con contribuciones menores a nivel electrónico, este efecto viene determinado por la coordinación estabilizante del sustituyente en orto al Cu durante el estado de transición y por la carga estérica, que aumentan el estado energético del haloareno. El Capítulo 4 describe los estudios teóricos sobre las propiedades electrónicas del grupo –CF3 en química orgánica y organometálica. Evidentemente, este tema es muy importante para entender los mecanismos de reacción y para el desarrollo de la investigación de reacciones de trifluorometilación mediadas por metales.
Organic compounds bearing a CF3 substituent, especially on an aromatic ring are in exceedingly high demand as building blocks for the needs of the agrochemical, pharmaceutical, and materials industries. While considerable progress has been made in the area of Cu-mediated aromatic trifluoromethylation, surprisingly little has been done in order to understand its mechanism. In this Thesis, we report the first combined experimental and computational studies aimed specifically at the elucidation of the mechanism of trifluoromethylation of haloarenes. The CuCF3 reagent used in our work was prepared by the new reaction of direct cupration of fluoroform, recently discovered by our group. As this remarkable transformation is unprecedented itself, we performed detailed studies of its mechanism as described in Chapter 1. It was found that the potassium counterion plays a crucial role in the Cu-CF3 bond formation. Addition of a ligand with high affinity to K+ results in significant inhibition of the cupration process. Chapter 2 reports a broad mechanistic investigation of trifluoromethylation of aryl halides which revealed a nonradical mechanism involving Ar-Hal oxidative addition to the Cu(I) center as the rate determining step. Chapter 3 deals with a long-known yet poorly understood accelerating effect of the ortho-substituent in Cu-promoted coupling reactions. With minor contributions from electronic factors, this effect is largely determined by the stabilizing coordination of the ortho-substituent to Cu in the transition state and the steric bulk that raises the energy of the haloarene. Chapter 4 describes our theoretical studies of the unusual electronic properties of the CF3 group in organic and organometallic chemistry. Evidently, this subject matter is highly relevant to understanding the reaction mechanisms and further development in the area of metal-mediated trifluoromethylation reactions.

This thesis focuses on the study of the life of a fluorescent dye. It also examines changes in its emission spectrum determined with the aid of development of fluorescence intensity over the long term sensing in several kinds if of cella. The general part of the thesis with the issues of confocal microscopy, fluorescent radiation and maks. Furthermorer, an analysis of methods for measuring fluorescence lifetime is done. In the thesis there is elaborated a description of the program, whitch was designed for the analysis of the collected output of the used confocal microscope. Sebsequently, the results are evaluated.

Phase transitions and other intrinsic properties (shape, size, architecture) of molecularly structured aerosol particles are important for understanding their role in planetary atmospheres and for technical applications. By combining bath gas cooling with time resolved mid-infrared spectroscopy and modeling, information is obtained on dynamic processes and intrinsic properties of fluoroform and ethane aerosol particles. The distinct infrared spectral features of fluoroform aerosol particles make it a particularly suitable model system. Homogeneous crystallization rates of the sub-micron sized aerosol particles are determined (JV = 10⁸ - 10¹⁰ cm-³s-¹ or JS = 10³ – 10⁵ cm-²s-¹ at a temperature of T = 78 K), and the controversial question regarding volume versus surface nucleation in freezing aerosols is addressed. It is demonstrated that current state of the art measurements of droplet ensembles cannot distinguish between the two mechanisms due to inherent experimental uncertainties. The evolution of particle shape from spherical supercooled droplets to cube-like crystalline particles and eventually to elongated crystalline particles is recorded and analyzed in detail with the help of vibrational exciton model calculations. Phase behaviour of pure ethane aerosols and ethane aerosols formed in the presence of other ice nuclei under conditions mimicking Titan’s atmosphere provide evidence for the formation of supercooled liquid ethane aerosol droplets, which subsequently crystallize. The observed homogeneous freezing rates (JV = 10⁷ – 10⁹ cm-³s-¹) imply that supercooled ethane could play a similar role in ethane rich regions of Titan’s atmosphere as supercooled water does in the Earth’s atmosphere.

Introduzione I tumori colo-rettali sono attualmente la seconda causa oncologica di morte per entrambi i sessi. La stadiazione linfonodale è elemento dirimente la stadiazione oncologica e la prognosi dei pazienti, con la conseguente indicazione a trattamenti chemioterapici adiuvanti. Infatti pazienti con malattia linfonodale negativa (N0) hanno una Overall Survival a 5 anni del 70-80%, contro una percentuale del 30-60% nei pazienti N+ (va precisato però che la sopravvivenza in questo gruppo è migliorata dal trattamento chemioterapico adiuvanti). Nel 20-30% dei pazienti che presentano recidiva di malattia numerosi autori ipotizzano che questa possa essere dovuta a metastasi linfonodali occulte. Inoltre nella chirurgia oncologica colorettale, l’identificazione dei linfonodi sentinella permette la ricerca delle micrometastasi tramite la cosiddetta “ultrastadiazione” dei linfonodi campionati con sezioni seriate ed indagini immunoistochimiche o reverse transcriptase-polymerase chain reaction (procedure, per i cui costi e tempi, non applicabili su tutti i linfonodi). Dai dati riportati in letteratura, è stata evidenziata una prognosi peggiore nei pazienti pN0 affetti da micrometastasi ed è tuttora oggetto di dibattito la chemioterapia adiuvante in questi pazienti. Il verde indocianina è stato proposto nell’identificazione intraoperatoria dei linfonodi sentinella tramite Fluorescenza vicina all’infrarosso, come già validato nei tumori della mammella e del compartimento testa/collo e nel melanoma cutaneo. Materiali e metodi Sono stati inseriti nello studio i pazienti sottoposti a chirurgia colorettale per neoplasia presso il Dipartimento di Chirurgia Generale “P. Stefanini” dell’AOU Policlinico “Umberto I” di Roma e Dipartimento di Chirurgia Generale dell’Ospedale di Fidenza (AUSL di Parma). Come da protocollo, sul pezzo operatorio a fresco appena resecato, dopo apertura del viscere e identificazione del tumore, viene iniettato 1ml di colorante, su mucosa sana, equidistribuito sui quattro punti cardinali peritumorali. Dopo circa 5-7 minuti vengono identificate e prelevate le sedi di maggior fluorescenza sul tessuto linfoadiposo mesenteriale per essere sottoposte ad esami di ultrastadiazione. Per ogni paziente inoltre sono stati rilevati i dati dell’esame istologico, in particolare la correlazione con la stadiazione linfonodale in riferimento al linfonodo sentinella Risultati Nel corso di questo periodo 58 pazienti sono stati sottoposti a resezioni oncologiche colorettali VLS standard. In ogni paziente è stato identificato almeno 1 SLN. Dal campionamento di tutti pezzi operatori sono stati repertati 1085 linfonodi (117 SLN, media 2.01). Nei pazienti N0 sono stati trovati trovati 54 SLN (media 1,9). La detection rate e la sensitivity rate sono state del 94,8% (55/58 pts) e del 100% (30 SLN+ / 30 N+ pts) rispettivamente. La false negative rate è stata dello 0%. In questa serie preliminare, l’assetto istologico dei SLN (sia negli N+ che negli N0) ha correttamente predetto lo stato dei linfonodi loco-regionale. Dopo gli esami di ultrastadiazione, sono state riscontrate micrometastasi nei SLN N0 in 4 pazienti (14%, 4/28 NND pts) che sono stati così ri-stadiati come N1 ed inviati a trattamento chemioterapico adiuvante. Conclusioni Nella nostra serie preliminare, la mappatura NIRF dei SLN con tecnica ex-vivo ha predetto correttamente lo stato linfonodale loco-regionale, come confermato all’esame istologico. L’identificazione delle micrometastasi ha permesso a 4 pazienti precedentemente stadiati come N0 di beneficiare del trattamento chemioterapico adiuvante con l’obiettivo di ridurre il rischio di recidiva. Il colorante vitale verde di indocianina però risulta non ottimale per la ricerca dei linfonodi sentinella e vi è la necessità di sviluppare e testare nuovi fluorofori, nuovi software e hardware per migliorare, nel futuro, le mappature linfonodali.

Charles University in Prague Faculty of Pharmacy in Hradec Kralove Department of Pharmaceutical Chemistry and Drug Control Student: Eva Švandrlíková Supervisor: Doc. PharmDr. Petr Zimčík Ph.D. Title of the diploma thesis: Synthesis of magnesium(II) azaphthalocyanines as potential fluorophores Azaphthalocyanines are macrocyclic compounds, which can exist with or without central metal (i.e. metal-free). Central metal can be chosen from a wide range of cations leading to significant changes in photophysical and photochemical properties of the macrocycle. My work is focused on magnesium complexes because of their significant fluorescence. Magnesium azaphthalocyanines are generally synthesized by cyclotetramerization reaction with magnesium butoxide. However, some azaphthalocyanines may contain labile peripheral substituents that may be cleaved in butoxides or in the case of unsymmetrical azaphthalocyanines the separation must be performed in a metal-free form. For these reasons, my work concerns with direct magnesium insertion into already prepared azaphthalocyanine macrocycle. I investigated possibilities of direct magnesium insertion with different kinds of magnesium salts, in different solvents, under different dryness of solvent, different temperature and different peripheral substitution of the macrocycle....

The aim of the diploma thesis was to prepare and characterize fluorescence sensor systems based on fluorophores and supramolecular components - cyclodextrins - attached to solid supports. In this work, functionalized 75 µm glass beads and two types of Nafion membranes were used as negatively charged solid surfaces. Derivatives of naphthalimide with a positively charged part allowing the attachment to surfaces were synthesized. The positively charged naphthalimide derivative was then attached on negatively charged surfaces via electrostatic interactions and the binding to the solid supports was examined using UV-VIS spectroscopy. Alternatively, the positively charged β-cyclodextrin derivative was also attached to the surface in an equimolar ratio with PNI-HEMPDA. The focus of the work were measurements of fluorescence sensor responses in the gas and liquid phase to linear alcohols - methanol to n-hexanol - for all sensor systems. For the studied sensor systems, the selected sensor parameters were determined - sensitivity, the limit of detection, linear dynamic range and a sensor response time constant. A practical application of the novel sensor system for the detection of ethanol in gasoline was examined. Fluorescence sensor response measurements of the prepared systems based on naphthalimide and...