The Coumarin-Dimer Spring-The Struggle between Charge Transfer and Steric Interactions

Chemistry : a European Journal
Łukasz KielesińskiDaniel T Gryko

Abstract

The synthesis of a weakly coupled, strongly polarized coumarin dimer has been achieved for the first time. The three-step strategy comprises the Skattebøl formylation followed by the Knoevenagel reaction and the formation of a tertiary amide by using a peptide-type procedure. The molecule consists of two different coumarin moieties: One is a classical donor-acceptor system and the second one possesses a weaker amide donor at the 7-position. The polarized coumarin dimer can form an electronically conjugated structure possessing an electric dipole larger than that of 7-(dimethylamino)coumarin-3-carboxylic acid. The limited flexibility of the inter-coumarin connection results in stable conformers of different electric dipole moments and complex photophysics. In the solid state, this compound has a strongly bent conformation with the two coumarin units forming an angle of around 74°. In solution, two conformers are in equilibrium. The existence of the molecule as two conformers in the ground state has been confirmed by optical studies, and further corroborated by molecular calculations. The fluorescence spectra possess a unique feature: A charge-transfer band (ca. 550 nm) is visible only in nonpolar or weakly polar solvents. Optica...Continue Reading

References

Nov 19, 2004·Organic Letters·Krishnamoorthy SivakumarQian Wang
Apr 23, 2005·Angewandte Chemie·Herbert Meier
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Apr 25, 2008·Nature Materials·Sachio Horiuchi, Yoshinori Tokura
Feb 21, 2009·Chemistry : a European Journal·Andreas LohrFrank Würthner
Mar 17, 2009·Journal of the American Chemical Society·Pauline N Wyrembak, Andrew D Hamilton
Apr 2, 2009·Accounts of Chemical Research·Hwan Myung Kim, Bong Rae Cho
Jul 9, 2009·Angewandte Chemie·Andreas LohrFrank Würthner
May 19, 2010·The Journal of Physical Chemistry. B·Hui JinMark Maroncelli
Sep 17, 2010·Journal of Biological Engineering·Mark A Haidekker, Emmanuel A Theodorakis
May 10, 2011·Organic Letters·Gun-Joong KimHae-Jo Kim
May 25, 2011·Organic & Biomolecular Chemistry·Tiffany P GustafsonAndrei G Kutateladze
Nov 29, 2011·The Journal of Physical Chemistry. a·Xiaogang LiuAnita Zeidler
Aug 9, 2012·Chemical Reviews·Dan-Wei ZhangZhan-Ting Li
Feb 8, 2013·Organic & Biomolecular Chemistry·Marta Dal Molin, Stefan Matile
Sep 21, 2013·Journal of the American Chemical Society·Yufeng WangMarcus Weck
Sep 24, 2013·Organic & Biomolecular Chemistry·David Alonso Doval, Stefan Matile
Jan 16, 2014·Journal of the American Chemical Society·Laure SebaounIvan Huc
Jul 25, 2014·Physical Chemistry Chemical Physics : PCCP·Mariusz TasiorDaniel T Gryko
Aug 19, 2014·The Journal of Organic Chemistry·Mariusz TasiorDaniel T Gryko
Mar 25, 2015·Nature Chemistry·Alok S TayiSamuel I Stupp
Jul 23, 2015·Physical Chemistry Chemical Physics : PCCP·Andrzej L Sobolewski
Aug 28, 2015·Organic Letters·Marek K WęcławskiDaniel T Gryko
Sep 9, 2015·Chemistry : a European Journal·André Zitzler-KunkelFrank Würthner
Nov 21, 2015·Organic & Biomolecular Chemistry·Maria E Due-HansenTrond Ulven
Jun 16, 2016·Journal of the American Chemical Society·Makam PandeeswarT Govindaraju
Sep 13, 2016·Journal of the American Chemical Society·Anna PurcValentine I Vullev
Jul 1, 2015·Chemical Science·Subhankar SinghaKyo Han Ahn

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Citations

May 17, 2018·Physical Chemistry Chemical Physics : PCCP·Łukasz KielesińskiOlaf W Morawski
Jul 20, 2018·Chemistry, an Asian Journal·Marek K WęcławskiDaniel T Gryko
Apr 6, 2019·Physical Chemistry Chemical Physics : PCCP·Łukasz KielesińskiDaniel T Gryko
Apr 17, 2019·Chemistry : a European Journal·Rafał OrłowskiDaniel T Gryko
Sep 17, 2019·Chemistry : a European Journal·Łukasz KielesińskiOlaf Morawski
Sep 4, 2021·Organic Letters·Krzysztof GórskiDaniel T Gryko

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