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Circularly Polarized Luminescence of a Stereogenic Curved Paraphenylene Anchoring a Chiral Binaphthyl in Solution and Solid State
Author(s) -
Sato Kenta,
Hasegawa Masashi,
Nojima Yuki,
Hara Nobuyuki,
Nishiuchi Tomohiko,
Imai Yoshitane,
Mazaki Yasuhiro
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202004283
Subject(s) - luminescence , materials science , stereocenter , delocalized electron , excited state , exciton , quantum yield , chirality (physics) , dipole , transition dipole moment , crystallography , fluorescence , molecular physics , photochemistry , optoelectronics , optics , condensed matter physics , atomic physics , chemistry , physics , organic chemistry , chiral symmetry breaking , quantum mechanics , quark , nambu–jona lasinio model , enantioselective synthesis , catalysis
A curved stereogenic [6]paraphenylene ([6]PP), anchoring a chiral binaphthyl scaffold at 7,7’‐positions, was prepared and investigated for its properties as a solid‐state circularly polarized luminescence (CPL) dye. X‐ray analysis revealed a helically twisted structure of PP units induced by axial chirality of binaphthyl framework. The curved [6]PP exhibits fluorescence in powder and polymethyl methacrylate (PMMA) film as well as solution. A significant increase in quantum yield was observed for a non‐fluid PMMA film owing the suppression of the molecular motion. The g CPL values of the dye in solution and as PMMA film were almost the same (4.3–4.4×10 −3 ) and lager than that in powder. TD‐DFT calculations in the excited state suggest that the exciton can be delocalized into a twisted PP unit to produce a larger magnetic transition dipole moment.