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Carborane‐Induced Excimer Emission of Severely Twisted Bis‐ o ‐Carboranyl Chrysene
Author(s) -
Marsh Adam V.,
Cheetham Nathan J.,
Little Mark,
Dyson Matthew,
White Andrew J. P.,
Beavis Peter,
Warriner Colin N.,
Swain Anthony C.,
Stavrinou Paul N.,
Heeney Martin
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201805967
Subject(s) - chrysene , excimer , chemistry , carborane , excited state , photochemistry , photoluminescence , molecule , fluorescence , stereochemistry , materials science , organic chemistry , atomic physics , anthracene , physics , quantum mechanics , optoelectronics
The synthesis of a highly twisted chrysene derivative incorporating two electron deficient o ‐carboranyl groups is reported. The molecule exhibits a complex, excitation‐dependent photoluminescence, including aggregation‐induced emission (AIE) with good quantum efficiency and an exceptionally long singlet excited state lifetime. Through a combination of detailed optical studies and theoretical calculations, the excited state species are identified, including an unusual excimer induced by the presence of o ‐carborane. This is the first time that o ‐carborane has been shown to induce excimer formation ab initio, as well as the first observation of excimer emission by a chrysene‐based small molecule in solution. Bis‐ o ‐carboranyl chrysene is thus an initial member of a new family of o ‐carboranyl phenacenes exhibiting a novel architecture for highly‐efficient multi‐luminescent fluorophores.