Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 70, Issue 16, Pages 6313-6320Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo050766n
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A donor-acceptor dyad system involving tetrathiafulvalene (TTF) as donor attached by a flexible spacer to perylene-3,4:9,10-bis(dicarboximide) (PDI) as acceptor was synthesized and characterized. The strategy used the preliminary synthesis of an unsymmetrical PDI unit bearing an alcohol functionality as anchor group. Single-crystal analysis revealed a highly organized arrangement in which all PDI molecules are packed in a noncentrosymmetrical pattern. It was shown that the fluorescence emission intensity of the TTF-PDI dyad can be reversibly tuned depending on the oxidation states of the TTF unit. This behavior is attributed to peculiar properties of TTF linked to a PDI acceptor, which fluoresces intrinsically. Consequently, this dyad can be considered as a new reversible fluorescence-redox dependent molecular system.
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