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Synthesis and properties of tetrathiafulvalene-porphyrin assemblies

Meijiang LI, Rui HUANG, Changzhi WU, Hujin ZUO, Guoqiao LAI, Yongjia SHEN

《化学科学与工程前沿（英文）》 2011年第5卷第4期页码 422-428 doi: 10.1007/s11705-011-1124-x

摘要： Two donor-σ-acceptor molecular systems incorporating tetrathiafulvalene (TTF) and tetraphenylporphyrin (TPP) units, TTF-TPP ( ) and TTF-TPP-TTF ( ), were synthesized. Both and and their synthetic intermediates have been characterized by H nuclear magnetic resonance ( H NMR) and mass spectrography (MS). Their ultraviolet and visible spectroscopy (UV-Vis) and cyclic voltammetry (CV) showed negligible intramolecular charge transfer interaction in their ground states. Their fluorescence intensity was strongly quenched compared with TPP, which implied the photoinduced electron transfer occurred from the TTF unit to the TPP unit in the excited state. On the other hand, their fluorescence intensity could be modulated by sequential oxidation of the TTF unit using chemical methods, which exhibited their potential application in fluorescence molecular switch.

关键词： tetrathiafulvalene tetraphenylporphyrin dyad triad fluorescence molecular switch

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Synthesis, spectroscopic, and electrochemical properties of two dyads consisted of tetrathiafulvalene

Guoqiao LAI, Yibo LIU, Meijiang LI, Yongjia SHEN

《化学科学与工程前沿（英文）》 2009年第3卷第2期页码 192-195 doi: 10.1007/s11705-009-0015-x

摘要： Two donor-σ-acceptor molecules containing tetrathiafulvalene (TTF) and carbazole moieties were synthesized by the reaction of 9-(4-bromo-butyl)-carbazole ( ) with 2,6-bis(hexylthio)-3-(2-cyanoethylthio)-7-(methylthio)-tetrathiafulvalene ( ) or 2,6-bis(2-cyanoethylthio)-3,7-bis(methylthio)tetrathiafulvalene ( ) in the presence of CsOH·H O, respectively. The structures of the molecules were characterized by H NMR, C NMR, MS, and elemental analyses. They showed negligible intramolecular charge-transfer interaction in their ground states as indicated by their UV-Vis spectroscopics and cyclic voltammetry results. Compared with carbazole, their fluorescence was strongly quenched, which implied that a photo induced electron transfer (PET) interaction between TTF and carbazole moieties occurred.

关键词： donor-σ-acceptor molecule intramolecular charge transfer interaction photo induced electron transfer tetrathiafulvalene carbazole

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Synthesis and properties of tetrathiafulvalene-fluorescein dyads

Guoqiao LAI, Yibo LIU, Yu ZHANG, Jun RUAN, Meijiang LI, Yongjia SHEN

《化学科学与工程前沿（英文）》 2009年第3卷第3期页码 314-317 doi: 10.1007/s11705-009-0207-4

摘要： Two donor-acceptor molecular systems consisted of tetrathiafulvalene (TTF) and fluorescein were designed and synthesized. The target compounds and their key intermediates were characterized by H NMR, mass spectrography, and infrared spectroscopy, respectively. The UV-vis spectra implied intramolecular interaction in their ground state. Fluorescence spectra and fluorescence lifetimes indicated the photoinduced charge transfer (PET) interaction between the TTF and fluorescein units in their excited states.

关键词： TTF fluorescein charge transfer