Synthesis and tunability of highly electron-accepting, N-benzylated "phosphaviologens"

Journal of the American Chemical Society
Monika StolarThomas Baumgartner

Abstract

We report a structure-property study on phosphoryl-bridged viologen analogues with a remarkably low reduction threshold. Utilizing different benzyl groups for N-quaternization, we were able to confirm the p-benzyl substituent effect on the electronic tunability of the system while maintaining the characteristic chromic response of viologens with two fully reversible one-electron reductions. Due to the considerably increased electron-acceptor properties of the phosphoryl-bridged bipyridine precursor, N-benzylation was found to be very challenging and required the development of new synthetic strategies toward the target viologen species. This study also introduces a new and convenient way for the anion exchange of viologen systems by utilizing methyl triflate. Finally, the practical utility of the new species was verified in simplified proof-of-concept electrochromic devices.

References

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Dec 1, 2006·The Journal of Physical Chemistry. B·Mahesh HariharanDanaboyina Ramaiah
Jun 17, 2011·Inorganic Chemistry·Stefan Durben, Thomas Baumgartner
Mar 15, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Yi Ren, Thomas Baumgartner
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May 16, 2013·Physical Chemistry Chemical Physics : PCCP·Monika Stolar, Thomas Baumgartner
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Mar 29, 2014·Chemistry, an Asian Journal·Monika Stolar, Thomas Baumgartner

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Citations

Sep 2, 2015·Journal of the American Chemical Society·Christian ReusThomas Baumgartner
Mar 30, 2016·Annual Review of Chemical and Biomolecular Engineering·Yang WangDelia J Milliron
Jan 14, 2017·ACS Applied Materials & Interfaces·Teng GongEn-Qing Gao
Jan 12, 2017·Chemistry : a European Journal·Tobias W GreulichArmido Studer
May 10, 2017·Journal of the American Chemical Society·Alexis N WoodwardMichael G Walter
Jun 9, 2016·Chemistry : a European Journal·Muhammad Anwar Shameem, Andreas Orthaber
Nov 18, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Keyhan EsfandiarfardSascha Ott
Aug 20, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Christian Reus, Thomas Baumgartner
Jun 2, 2017·Chemistry : a European Journal·Philip HindenbergCarlos Romero-Nieto
Mar 9, 2018·Chemical Communications : Chem Comm·Monika Stolar, Thomas Baumgartner
Aug 18, 2017·Chemistry : a European Journal·Laura Striepe, Thomas Baumgartner
May 20, 2020·Chemical Communications : Chem Comm·Toshiki FujiiKensuke Naka
Mar 12, 2020·Chemistry : a European Journal·Thomas DelouchePierre-Antoine Bouit
Jan 31, 2018·Nanoscale·Yanling ZhaiShaojun Dong
Dec 12, 2018·Organic Letters·Mathilde BervilleJean Weiss
May 1, 2020·The Journal of Organic Chemistry·Robin SchoemakerJan J Weigand
May 10, 2019·The Journal of Physical Chemistry. B·Santhanamoorthi NachimuthuJyh-Chiang Jiang
Mar 8, 2018·The Journal of Organic Chemistry·Tomohiro HigashinoHiroshi Imahori

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