Synthesis and properties of tetrathiafulvalene-porphyrin assemblies

2011, Volume 5, Issue 4

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

Synthesis and properties of tetrathiafulvalene-porphyrin assemblies

1. Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 310012, China; 2. Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science & Technology, Shanghai 200237, China

Available online: 2011-12-05

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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

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