Stabilizing Pentacene By Cyclopentannulation

Angewandte Chemie
Sambasiva R BheemireddyKyle N Plunkett

Abstract

A new class of stabilized pentacene derivatives with externally fused five-membered rings are prepared by means of a key palladium-catalyzed cyclopentannulation step. The target compounds are synthesized by chemical manipulation of a partially saturated 6,13-dibromopentacene precursor that can be fully aromatized in a final step through a DDQ-mediated dehydrogenation reaction (DDQ=2,3-dichloro-5,6-dicyano-1,4-benzoquinone). The new 1,2,8,9-tetraaryldicyclopenta[fg,qr]pentacene derivatives have narrow energy gaps of circa 1.2 eV and behave as strong electron acceptors with lowest unoccupied molecular orbital energies between -3.81 and -3.90 eV. Photodegradation studies reveal the new compounds are more photostable than 6,13-bis(triisopropylsilylethynyl)pentacene (TIPS-pentacene).

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Citations

Aug 26, 2016·The Journal of Organic Chemistry·Bingxin YuanKyle N Plunkett
Apr 4, 2017·Journal of the American Chemical Society·Sambasiva R BheemireddyKyle N Plunkett
Feb 24, 2017·Chemistry : a European Journal·Kamal SbargoudMichel Frigoli
Jul 19, 2016·Chemistry : a European Journal·Gang ZhangMichael Mastalerz
Aug 3, 2018·Angewandte Chemie·Ben-Lin HuMartin Baumgarten
Dec 2, 2018·Chemical Communications : Chem Comm·Sambasiva R BheemireddyKyle N Plunkett
Nov 27, 2018·Chemistry : a European Journal·Narcisse UkwitegetseMark E Thompson
Nov 23, 2018·Chemistry : a European Journal·Wenlong YangWesley A Chalifoux
Feb 15, 2019·Chemistry, an Asian Journal·Thomas B J HallNigel T Lucas
May 21, 2019·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Cyril Aumaitre, Jean-François Morin
Jul 30, 2020·Angewandte Chemie·Hong WangFrancis D'Souza
May 6, 2019·Chemistry : a European Journal·Taichi KoikeTakeaki Iwamoto
Jul 3, 2019·Angewandte Chemie·Anthony JollyJean-François Morin
May 13, 2020·Beilstein Journal of Organic Chemistry·Ji MaXinliang Feng
Jul 28, 2017·European Journal of Organic Chemistry·Ruth Dorel, Antonio M Echavarren
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May 22, 2021·Organic & Biomolecular Chemistry·Sarasija DasSanjio S Zade
Jan 24, 2018·The Journal of Organic Chemistry·Lafe J PurvisChristopher J Douglas
Jan 5, 2021·The Journal of Organic Chemistry·Yachu DuKyle N Plunkett
Jul 13, 2019·Journal of the American Chemical Society·Junzhi LiuXinliang Feng
Aug 15, 2021·Chemistry, an Asian Journal·Ming Hui ChuaJianwei Xu

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