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Synthesis, Optical Properties, and Crystal Structure of 1,4‐Dipropyltetracene
Author(s) -
Kitamura Chitoshi,
Matsumoto Chika,
Yoneda Akio,
Kobayashi Takashi,
Naito Hiroyoshi,
Komatsu Toshiki
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000112
Subject(s) - chemistry , tetracene , alkyl , stacking , hexane , solid state , crystal structure , molecule , crystallography , absorption spectroscopy , absorption (acoustics) , fluorescence , photochemistry , stereochemistry , organic chemistry , physics , quantum mechanics , acoustics
We synthesized 1,4‐dipropyltetracene on a 200‐mg scale, the key step of which involved a Diels–Alder reaction between alkyl‐substituted o ‐quinodimethane, generated in situ, and 1,4‐naphthoquinone. The product was obtained as an orange solid, which was soluble in organic solvents including hexane. The optical properties of the product in solution showed no marked differences from those of other 1,4,7,10‐tetraalkyltetracenes. Solid‐state absorption and fluorescence spectra exhibited 20–30 nm blueshifts compared with those of 1,4,7,10‐tetrapropyltetracene. X‐ray analysis revealed that two propyl groups were coplanar with the tetracene ring, that there was no π overlap along the stacking direction, and that the molecules formed a herringbone structure. The peripheral alkyl chains were found to be important for controlling the molecular packing and optical properties in the solid state.