Synthesis and properties of tetrathiafulvalene-porphyrin assemblies

Abstract

Two donor-σ-acceptor molecular systems incorporating tetrathiafulvalene (TTF) and tetraphenylporphyrin (TPP) units, TTF-TPP (dyad 1) and TTF-TPP-TTF (triad 2), were synthesized. Both dyad 1 and triad 2 and their synthetic intermediates have been characterized by ¹H nuclear magnetic resonance (¹H 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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Acknowledgments

This work was supported by the National Natural Science Foundation of China (Grant Nos. 21076078 and 20676036).

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2014 Higher Education Press and Springer-Verlag Berlin Heidelberg