Bismetal Complexes of 5,20-Bis(5-formyl-2-pyrrolyl)-[26]hexaphyrin(1.1.1.1.1.1) Exhibiting Strong Near-Infrared Region Absorptions

Chemistry : a European Journal
Hirotaka Mori, Atsuhiro Osuka

Abstract

[26]Hexaphyrin(1.1.1.1.1.1) bearing two 5-formyl-2-pyrrolyl groups at the 5- and 20-positions was prepared by cross-condensation of 5,10-bis(pentafluorophenyl)-substituted tripyrrane with 2,5-diformylpyrrole as an effective binuclear metal-coordinating ligand, owing to the two hemiporphyrin-like NNNN pockets. In fact, metalation of this hexaphyrin with Zn(II) , Cu(II) , and Pd(II) salts proceed smoothly at room temperature to give the corresponding bismetal complexes that displayed remarkably redshifted absorption spectra reaching deep into near infrared region. These redshifted absorption bands are ascribed, through electrochemical investigations and DFT calculations, to two structural motifs: the N-metalopyrrole substructure that elevates the HOMO level due to the electron-donating property and the two coordinated metal ions that serve as Lewis acids to lower the LUMO level.

References

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Feb 19, 2002·Chemical Reviews·Ayub Jasat, David Dolphin
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Oct 7, 2006·Chemistry : a European Journal·Masaaki Suzuki, Atsuhiro Osuka
Jun 4, 2010·Angewandte Chemie·Tomohiro HigashinoAtsuhiro Osuka
Mar 16, 2011·Chemical Communications : Chem Comm·Atsuhiro Osuka, Shohei Saito
Apr 15, 2011·Angewandte Chemie·Shohei Saito, Atsuhiro Osuka
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Feb 18, 2012·Chemistry, an Asian Journal·Takayuki TanakaAtsuhiro Osuka
Aug 7, 2012·Angewandte Chemie·Koji NaodaAtsuhiro Osuka
Apr 26, 2013·Chemistry, an Asian Journal·Koji NaodaAtsuhiro Osuka

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Citations

Aug 19, 2016·Chemical Reviews·Takayuki Tanaka, Atsuhiro Osuka
Mar 27, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·James T BrewsterJonathan L Sessler
Oct 16, 2015·Chemistry : a European Journal·Mercedes AlonsoFrank De Proft
Sep 14, 2017·Journal of the American Chemical Society·Hervé RuffinStéphane Le Gac
Feb 23, 2017·Chemical Reviews·Bartosz SzyszkoLechosław Latos-Grażyński

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