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2009, Volume 3, Issue 2

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Frontiers of Chemical Science and Engineering >> 2009, Volume 3, Issue 2 doi: 10.1007/s11705-009-0015-x

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

1. Key Lab 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: 2009-06-05
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Abstract

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.

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