Combined Experimental and Theoretical Study on Circular Dichroism and Circularly Polarized Luminescence of Configurationally Robust D3 -Symmetric Triple Pentahelicene

The Journal of Physical Chemistry. a
Hiroki TanakaTadashi Mori

Abstract

Pentahelicene (PH) exhibits the largest absorption ( gabs) and luminescence ( glum) dissymmetry factors among the helicene family but is configurationally and (photo)chemically labile, encumbering its application to chiroptical materials. To bypass the pitfalls, three PH units are merged in a single molecule to build D3-symmetric triple pentahelicene, hexabenzotriphenylene (HBT), which attains indeed the configurational and (photo)chemical robustness through equilibrium with a C2-symmetric conformer that interrupts the racemization and photocyclization. UV-vis, circular dichroism (CD), and circularly polarized luminescence (CPL) spectral examinations reveal the significantly larger gabs and glum values for HBT than for any of configurationally robust single [ n]helicene ( n ≥ 6) and C2-symmetric triple pentahelicene, trinaphthotriphenylene (TNT). Theoretical calculations precisely reproduce the main features of the experimental CD and CPL spectra of PH, HBT, and TNT, and the relevant electric and magnetic transition moments and their mutual angles well rationalize the relative CD and CPL intensities of all the single and triple pentahelicenes.

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Citations

May 28, 2020·Chemistry : a European Journal·Kenichi Kato, Atsuhiro Osuka
Aug 23, 2019·Chemical Communications : Chem Comm·Pablo ReineJuan M Cuerva
Oct 12, 2019·Chemical Communications : Chem Comm·Wen-Long ZhaoChuan-Feng Chen
Jul 30, 2020·Chemistry : a European Journal·Lorenzo ArricoFrancesco Zinna
Feb 4, 2021·Organic Letters·Ryo TakishimaMasahiro Miura
Apr 4, 2020·Journal of the American Chemical Society·Nathaniel J SchusterColin Nuckolls
Jul 13, 2021·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Hayato TodaYoshitane Imai
May 3, 2019·The Journal of Physical Chemistry. a·Tal Aharon, Marco Caricato

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