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Synthesis and Crystallochromy of 1,4,7,10‐Tetraalkyltetracenes: Tuning of Solid‐State Optical Properties of Tetracenes by Alkyl Side‐Chain Length
Author(s) -
Kitamura Chitoshi,
Abe Yasushi,
Ohara Takuya,
Yoneda Akio,
Kawase Takeshi,
Kobayashi Takashi,
Naito Hiroyoshi,
Komatsu Toshiki
Publication year - 2010
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.200901668
Subject(s) - alkyl , solid state , side chain , crystal structure , derivative (finance) , chemistry , exciton , crystallography , planar , crystal (programming language) , orange (colour) , stereochemistry , polymer chemistry , materials science , organic chemistry , polymer , physics , condensed matter physics , computer graphics (images) , computer science , financial economics , programming language , economics , food science
We synthesized a series of 1,4,7,10‐tetraalkyltetracenes using a new 2,6‐naphthodiyne precursor and 2,5‐dialkylfurans as starting materials (alkyl=methyl to hexyl). Surprisingly, the solid‐state color of the tetracenes ranges through yellow, orange, and red. Both yellow and red solids are obtained for the butyl derivative. Optical properties in solution show no marked differences; however, those in the solid state show characteristics that vary with alkyl side‐chain length: methyl, propyl, and pentyl derivatives are orange; ethyl and butyl derivatives are yellow; and another butyl and hexyl derivative are red. X‐ray analyses reveal that the molecular structures are planar, semi‐chair, or chair forms; the chair form takes a herringbone‐like arrangement and the other forms take slipped parallel arrangements. The mechanism of crystallochromy is discussed in terms of molecular structure, crystal packing, and calculations that take account of exciton coupling.