Structural control of the electronic properties of photodynamic azobenzene-derivatized pi-conjugated oligothiophenes

The Journal of Physical Chemistry. a
Bruno JousselmeJean Roncali

Abstract

Quaterthiophenes containing a median 3,3'-dimethoxybithiophene (4MTZ) or bis(3,4-ethylenedioxythiophene) (4ETZ) block and an azobenzene group attached at two internal beta-positions of the end thiophene rings have been synthesized. The analysis of the crystal structure of the two compounds by X-ray diffraction shows that, for 4MTZ, the quaterthiophene chain adopts a syn-anti-syn conformation similar to the parent system based on unsubstituted quaterthiophene. In contrast, 4ETZ presents an all-anti conformation stabilized by noncovalent intramolecular interactions between oxygen atoms and thiophenic sulfur atoms. The effect of the photoisomerization of the azobenzene group on the electronic properties of the attached pi-conjugated quaterthiophene chain has been analyzed by UV-vis spectroscopy and cyclic voltammetry. The results obtained for 4MTZ suggest very limited geometrical changes due to the restricted rotation around the central interannular single bond caused by steric interactions between the methoxy groups. In contrast, upon trans to cis photoisomerization of the attached azobenzene group of 4ETZ, the quaterthiophene chain undergoes a reversible conformational switch to a final state with a lower HOMO level and a larger...Continue Reading

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Citations

May 21, 2010·Chemical Communications : Chem Comm·Sandrine KarpeJean Roncali
Jun 5, 2008·Chemistry : a European Journal·Truong Khoa TranDominique Vuillaume
Jan 29, 2011·Chemistry : a European Journal·Kazuto TakaishiMasanobu Uchiyama
Jun 21, 2013·Angewandte Chemie·Gebhard HaberhauerDieter Bläser
Feb 16, 2011·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Kazuto Takaishi, Masuki Kawamoto
Feb 27, 2010·Angewandte Chemie·Gebhard Haberhauer, Christine Kallweit
Dec 14, 2011·Organic Letters·Kazuto TakaishiMasanobu Uchiyama
Aug 5, 2011·The Journal of Organic Chemistry·Kazuto TakaishiMasanobu Uchiyama
Dec 21, 2006·Journal of the American Chemical Society·Dorothee WasserbergPeter Bäuerle

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