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Engineering Stacks of V‐Shaped Polyaromatic Compounds with Alkyl Chains for Enhanced Emission in the Solid State
Author(s) -
Sekiguchi Shoya,
Kondo Kei,
Sei Yoshihisa,
Akita Munetaka,
Yoshizawa Michito
Publication year - 2016
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.201602502
Subject(s) - anthracene , fluorescence , solid state , alkyl , materials science , derivative (finance) , photochemistry , chemistry , organic chemistry , optics , physics , financial economics , economics
A V‐shaped bisanthracene derivative with three butyl groups formed two types of emissive solids that display bluish green and blue fluorescence (Φ F =72 and 32 %, respectively), depending on the preparation conditions. The crystal and powder X‐ray analyses reveal that the highly emissive solid adopts a head‐to‐head arrangement with discrete stacks of the anthracene moieties, whereas the moderately emissive solid adopts a head‐to‐tail arrangement without the stacks. The obtained molecular arrangements are transformed by thermal stimuli accompanying the change in fluorescence. Furthermore, large enhancements of dye emissions (12–45‐fold) through highly efficient host–guest energy transfer were achieved in the solid state by adding minute amounts of various fluorescent dyes (e.g. rubrene and Nile red) to the V‐shaped compound.