2,2](5,8)Picenophanedienes: Syntheses, Structural Analyses, Molecular Dynamics, and Reversible Intramolecular Structure Conversion

Journal of the American Chemical Society
Min-Chih TangYao-Ting Wu

Abstract

This study presents an important and efficient synthetic approach to 5,8-dibromo-2,11-di-tert-butylpicene (3), with multigram scale, which was then converted to a new series of picenophanes (6-10). The tub-shaped [2,2](5,8)picenophanediene 8 with two cis-ethylene linkers was explored using X-ray crystallography. The tub-to-tub inversion proceed through the successive bending of the linkers and the barrier for isopropyl-substituted derivative 10 was experimentally estimated to be 18.7 kcal/mol. Picenophanes with a large π-system and semi-rigid structure exhibited anomalous photophysical properties. The ethano-bridged picenophane shows the weak exciton delocalization while the cis-ethylene-bridged picenophane exhibits dual emission rendered by the weakly delocalized exciton and excimer. With the aid of the ultrafast time-resolved emission spectroscopy, the mechanism of the excimer formation is resolved, showing a unique behavior of two-state reversible reaction with fast structural deformation whose lifetime is around 20 ps at 298 K. This work demonstrates that the slight difference in the bridge of tub-shaped picenophanes renders distinct photophysical behavior, revealing the potential of harnessing inter-moiety reaction in the ...Continue Reading

References

Mar 14, 2007·Journal of the American Chemical Society·Andrzej SygulaMarilyn M Olmstead
Mar 5, 2008·The Journal of Chemical Physics·Jeng-Da Chai, Martin Head-Gordon
Aug 13, 2009·Organic Letters·Sarah GorettaMarc Gingras
Jun 1, 2013·Journal of the American Chemical Society·Chunxue YuanShigehiro Yamaguchi
Jun 25, 2013·Angewandte Chemie·Chieh-Ning FengYao-Ting Wu
Mar 13, 2014·Chemistry : a European Journal·Robert W MillerAdam C Whalley
May 30, 2015·Chemical Society Reviews·Parisa Ghods GhasemabadiGraham J Bodwell
Jul 5, 2016·Nature Communications·Shohei SaitoShigehiro Yamaguchi
Feb 22, 2017·Journal of the American Chemical Society·Christopher C McAteeCorinna S Schindler
May 4, 2017·Chemical Society Reviews·Zhichang LiuJ Fraser Stoddart
May 12, 2018·Journal of the American Chemical Society·Takuya YamakadoShohei Saito
Jul 24, 2018·Journal of the American Chemical Society·Guillaume PovieKenichiro Itami
May 28, 2019·Journal of the American Chemical Society·Sai Ho PunQian Miao

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