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Synthesis, Structure and Photophysical Properties of Pyrene–based [5]Helicenes: an Experimental and Theoretical Study
Author(s) -
Wang ChuanZeng,
Kihara Rie,
Feng Xing,
Thuéry Pierre,
Redshaw Carl,
Yamato Takehiko
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601327
Subject(s) - pyrene , density functional theory , molecular orbital , intramolecular force , homo/lumo , chemistry , photochemistry , atomic orbital , materials science , computational chemistry , molecule , organic chemistry , physics , quantum mechanics , electron
Pyrene‐cored [5]helicenes were prepared by a facile, efficient Wittig reaction and an intramolecular photocyclization reaction utilising 2,7‐di‐ tert ‐butylpyrene‐4‐carbaldehyde and naphthalene/pyrene‐based phosphorus ylides. Optical properties based on UV−vis absorption and fluorescence spectra were investigated. X‐ray crystallography revealed that the pyrene‐based [5]helicenes exhibited strong face‐to‐face π−π interactions and edge‐to‐face π−π interactions. HOMO and LUMO energies and molecular orbitals were also studied by density functional theory (DFT) calculations. This study has revealed that the torsion angle of the helical structure plays a role in determining the π−π interactions and the frontier molecular orbital energy levels. Thus, pyrene‐based helicenes need to be considered when one designs new highly efficient organic light‐emitting diodes and organic semiconductor materials.