Trans-A2B-corroles bearing a coumarin moiety--from synthesis to photophysics

Chemistry, an Asian Journal
Mariusz TasiorLucia Flamigni

Abstract

Four dyads comprised of corrole and coumarin units have been synthesised. Three coumarincarboxaldehydes were synthesized and transformed into the corresponding trans-A(2)B-corroles by reaction with 5-(pentafluorophenyl)dipyrromethane. It has been proven that this type of direct condensation can lead to the corresponding corroles in moderate yields. The reaction of hydroxybenzaldehydes with vinylphosphonium salts has been identified as the most general method for the preparation of formyl-coumarins with various patterns of substituents. The dyad consisting of ketobiscoumarin and corrole was synthesized by Sonogashira coupling. Spectroscopic and photophysical investigations revealed that there is an efficient energy transfer from the coumarin moiety to corrole in all four dyads. Energy transfer can be clearly ascribed to a dipole-dipole mechanism (Förster) for all dyads that contain luminescent coumarins and to an electron exchange mechanism (Dexter) for the dyad with the non-luminescent one. In the case of the dyad that bears coumarin with a hydroxy group at position 5, an electron-transfer was detected from corrole to coumarin. The latter process is possible because of the suitably low reduction potential of coumarins of this t...Continue Reading

References

Nov 15, 2000·The Journal of Organic Chemistry·P D RaoJ S Lindsey
Feb 15, 2001·Accounts of Chemical Research·D GustA L Moore
Jun 9, 2001·The Journal of Organic Chemistry·D T Gryko, K Jadach
Jun 30, 2001·The Journal of Organic Chemistry·R PaolesseR G Khoury
Sep 20, 2001·Journal of the American Chemical Society·B RamdhanieD P Goldberg
Oct 30, 2001·Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry·Z Gross
Dec 12, 2001·Inorganic Chemistry·A E Meier-CallahanZ Gross
Jun 20, 2002·Journal of the American Chemical Society·Irena SaltsmanZeev Gross
Oct 3, 2002·Journal of the American Chemical Society·Jason M SerinJean M J Fréchet
Feb 22, 2003·Chemistry : a European Journal·Roberto PaolesseMaria Graça H Vicente
Apr 30, 2004·Chemical Communications : Chem Comm·Christophe JeandonHenry J Callot
Jun 8, 2004·Magnetic Resonance in Chemistry : MRC·Yael S BalazsZeev Gross
Jun 18, 2004·Combinatorial Chemistry & High Throughput Screening·Jerzy RadeckiJanez Plavec
Jul 15, 2004·Dalton Transactions : an International Journal of Inorganic Chemistry·Jean-Michel BarbeRoger Guilard
Nov 6, 2004·The Journal of Organic Chemistry·Arumugasamy ElangovanTong-Ing Ho
Nov 19, 2004·Organic Letters·Krishnamoorthy SivakumarQian Wang
Mar 3, 2005·Journal of the American Chemical Society·Atif Mahammed, Zeev Gross
Apr 28, 2005·The Journal of Investigative Dermatology·David Denhardt
May 5, 2005·Journal of the American Chemical Society·Crisjoe A Joseph, Peter C Ford
May 10, 2005·Inorganic Chemistry·Nicola Y EdwardsMahdi M Abu-Omar
May 12, 2005·Chemical Communications : Chem Comm·James P CollmanChristopher J Sunderland
Sep 27, 2005·Inorganic Chemistry·James H Alstrum-AcevedoThomas J Meyer
May 6, 2006·The Journal of Organic Chemistry·Beata Koszarna, Daniel T Gryko
Jul 13, 2006·The Journal of Physical Chemistry. a·Tang DingChristopher J Ziegler
Sep 21, 2006·Journal of the American Chemical Society·Satoru HirotoAtsuhiro Osuka
Nov 30, 2006·Angewandte Chemie·Martin BröringMax C Holthausen
Jun 22, 2007·Accounts of Chemical Research·David P Goldberg
Aug 24, 2007·Chemical Communications : Chem Comm·Iris Aviv, Zeev Gross
Apr 7, 1989·Science·D Gust, T A Moore
Oct 11, 2007·Chemistry : a European Journal·Lucia FlamigniDaniel T Gryko
Apr 3, 2008·Chemistry : a European Journal·Lucia FlamigniPablo Ballester
Jun 12, 2008·Accounts of Chemical Research·Lucia FlamigniJean-Pierre Sauvage
Oct 8, 2008·Journal of the American Chemical Society·Francis D'SouzaShunichi Fukuzumi
Oct 28, 2008·The Journal of Physical Chemistry. B·Hiroshi Imahori
Mar 10, 2009·Inorganic Chemistry·Dorota KowalskaRonald P Steer
Mar 12, 2009·Chemical Communications : Chem Comm·Federica MandojRoberto Paolesse
May 26, 2009·Journal of the American Chemical Society·Amanda J McGownDavid P Goldberg
Jul 10, 2009·Chemical Society Reviews·Lucia Flamigni, Daniel T Gryko

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Citations

Aug 19, 2014·The Journal of Organic Chemistry·Mariusz TasiorDaniel T Gryko
Nov 19, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Biju BasumataryJeyaraman Sankar
Dec 8, 2010·Journal of Mass Spectrometry : JMS·Paweł SwiderWitold Danikiewicz
Feb 28, 2013·Chemistry, an Asian Journal·Adina I CiuciuDaniel T Gryko
Apr 14, 2015·Chemistry : a European Journal·Shota OoiAtsuhiro Osuka
Aug 5, 2015·The Journal of Physical Chemistry. a·Irena DeperasińskaBoleslaw Kozankiewicz
Feb 24, 2015·Physical Chemistry Chemical Physics : PCCP·Bartosz BursaDanuta Wróbel
Nov 5, 2016·Chemical Reviews·Rafał OrłowskiDaniel T Gryko
Oct 28, 2016·The Journal of Organic Chemistry·Rashid NazirDaniel T Gryko
Jul 25, 2014·Physical Chemistry Chemical Physics : PCCP·Mariusz TasiorDaniel T Gryko
Jul 6, 2014·Chemical Communications : Chem Comm·Marek K WęcławskiDaniel T Gryko
Jun 16, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ana F R CerqueiraAugusto C Tomé
Mar 23, 2018·Beilstein Journal of Organic Chemistry·Anna KuźnikBeata Fryczkowska
Nov 26, 2010·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Francesco NastasiMikalai Kruk
Apr 6, 2012·Chemical Communications : Chem Comm·Christopher J ZieglerVictor N Nemykin
Mar 31, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Lucia Flamigni
Apr 9, 2021·The Journal of Organic Chemistry·Łukasz KielesińskiDaniel T Gryko
Sep 19, 2012·The Journal of Physical Chemistry. a·Mikalai KrukWouter Maes
Feb 26, 2015·Inorganic Chemistry·Christopher M LemonDaniel G Nocera
Apr 29, 2014·The Journal of Physical Chemistry. a·Christophe GourlaouenLucia Flamigni
Mar 13, 2018·Organic Letters·Zhen GuoYefeng Tang

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