Comparative study on the structural, optical, and electrochemical properties of bithiophene-fused benzo[c]phospholes

Chemistry : a European Journal
Yoshihiro MatanoHiroshi Imahori

Abstract

Three types of bithiophene-fused benzo[c]phospholes were successfully prepared by Ti(II)-mediated cyclization of the corresponding dialkynylated bithiophene derivatives as a key step. Each sigma(3)-phosphorus center of the benzo[c]phosphole subunits was readily transformed into sigma(4)-phosphorus center by Au coordination or oxygenation. In addition, the bithiophene subunit was functionalized at the alpha,alpha'-carbon atoms by Pd-catalyzed cross-coupling reactions with heteroarylmetals and by an S(N)Ar reaction with hexafluorobenzene. The experimentally observed results (NMR spectroscopy, X-ray analysis, UV/Vis absorption/fluorescence spectroscopy, and cyclic/differential-pulse voltammetry) have revealed that the structural, optical, and electrochemical properties of the bithiophene-fused benzo[c]phospholes vary considerably depending on the pi-conjugation modes at the bithiophene subunits and the substituents of the heterocyclopentadiene components. The appropriately ring-annulated sigma(3)-P derivatives and sigma(4)-P-AuCl complexes were found to emit fluorescence in the orange-red region, and the sigma(4)-P-oxo derivatives proved to undergo reversible one-electron reduction at -1.4 to -1.8 V (vs ferrocene/ferrocenium). The...Continue Reading

References

Sep 15, 1988·Physical Review A: General Physics·A D Becke
Nov 17, 2001·Chemical Reviews·L Nyulászi
Aug 29, 2002·Chemical Communications : Chem Comm·Claire FaveRégis Réau
Apr 17, 2003·Angewandte Chemie·François Mathey
Aug 2, 2003·Journal of the American Chemical Society·Claire FaveRégis Réau
May 13, 2004·Journal of the American Chemical Society·Claire FaveRégis Réau
May 26, 2005·Chemistry : a European Journal·Thomas BaumgartnerLászló Nyulászi
Mar 7, 2006·Dalton Transactions : an International Journal of Inorganic Chemistry·Yvonne DienesThomas Baumgartner
Jul 15, 2006·The Journal of Organic Chemistry·Yoshihiro MatanoHiroshi Imahori
Nov 10, 2006·Chemical Reviews·Thomas Baumgartner, Régis Réau
Apr 24, 2007·Journal of Computational Chemistry·Run-Feng ChenWei Huang
Jul 13, 2007·The Journal of Organic Chemistry·Yoshihiro MatanoYoshifumi Kimura
Jul 21, 2007·BMJ : British Medical Journal·Clare Dyer
Jul 21, 2007·BMJ : British Medical Journal·Clare Dyer
Aug 10, 2007·Organic Letters·Takanobu SanjiMasato Tanaka
Jan 5, 2008·Organic & Biomolecular Chemistry·Bradley O Ashburn, Rich G Carter
Feb 12, 2008·Organic Letters·Aiko FukazawaShigehiro Yamaguchi

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Citations

Mar 28, 2017·Inorganic Chemistry·Arvind Kumar GuptaAndreas Orthaber
Sep 10, 2016·Angewandte Chemie·Tomohiro HigashinoHiroshi Imahori
Aug 20, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Christian Reus, Thomas Baumgartner
Jul 14, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Yoshinari KoyanagiYoshihiro Matano
Jun 2, 2017·Chemistry : a European Journal·Philip HindenbergCarlos Romero-Nieto
Dec 10, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·W DelaunayM Hissler
Nov 17, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Yoshinari KoyanagiYoshihiro Matano
Apr 17, 2018·Chemistry, an Asian Journal·Chenguang WangShigehiro Yamaguchi
Aug 4, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Elena OshchepkovaOlga Lodochnikova
Mar 27, 2015·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Yoshihiro Matano
Aug 28, 2009·Chemistry : a European Journal·Arihiro SaitoHiroshi Imahori
Aug 18, 2010·Chemistry : a European Journal·Omrane FadhelRégis Réau
Feb 4, 2011·Angewandte Chemie·Teruhisa TsuchimotoHiroshi Takahashi
Mar 21, 2009·Organic & Biomolecular Chemistry·Yoshihiro Matano, Hiroshi Imahori
Sep 5, 2012·Chemistry, an Asian Journal·David HanifiYi Liu
Jan 23, 2021·Inorganic Chemistry·Christina A BraunEric Rivard
Jun 17, 2011·Inorganic Chemistry·Stefan Durben, Thomas Baumgartner
Jan 8, 2011·Journal of the American Chemical Society·Yi Ren, Thomas Baumgartner
Mar 19, 2015·The Journal of Organic Chemistry·Motonobu TakahashiKyoko Nozaki
Feb 2, 2013·Organic Letters·Yoshihiro MatanoHiroshi Imahori

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