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dyad 1

fluorescence molecular switch 1

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Synthesis and properties of tetrathiafulvalene-porphyrin assemblies

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

Frontiers of Chemical Science and Engineering 2011, Volume 5, Issue 4, Pages 422-428 doi: 10.1007/s11705-011-1124-x

Abstract: 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.

Keywords： tetrathiafulvalene tetraphenylporphyrin dyad triad fluorescence molecular switch