Leroy-Lhez Stéphanie, Baffreau Jérôme, Perrin Lara, Levillain Eric, Allain Magali, Blesa Maria-Jesus, Hudhomme Piétrick
Chimie, Ingénierie Moléculaire et Matériaux d'Angers, UMR CNRS 6200 - Université d'Angers, 2 Bd Lavoisier, 49045 Angers, France.
J Org Chem. 2005 Aug 5;70(16):6313-20. doi: 10.1021/jo050766n.
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.
合成并表征了一种供体-受体二元体系，该体系以四硫富瓦烯（TTF）作为供体，通过柔性间隔基连接到苝-3,4:9,10-双（二甲酰亚胺）（PDI）作为受体。该策略采用了初步合成带有醇官能团作为锚定基团的不对称PDI单元。单晶分析揭示了一种高度有序的排列，其中所有PDI分子均以非中心对称模式堆积。结果表明，TTF-PDI二元体系的荧光发射强度可根据TTF单元的氧化态进行可逆调节。这种行为归因于与本征荧光的PDI受体相连的TTF的特殊性质。因此，该二元体系可被视为一种新型的可逆荧光-氧化还原依赖性分子体系。
