Synthesis and crystallochromy of 1,4,7,10-tetraalkyltetracenes: tuning of solid-state optical properties of tetracenes by alkyl side-chain length

Chemistry : a European Journal
Chitoshi KitamuraToshiki Komatsu

Abstract

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.

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Citations

Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online·Chitoshi KitamuraHiroyoshi Naito
Nov 8, 2011·Acta Crystallographica. Section E, Structure Reports Online·Chitoshi KitamuraHiroyoshi Naito
Sep 7, 2013·The Journal of Chemical Physics·Kazuhiro J Fujimoto, Chitoshi Kitamura
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Dec 16, 2016·The Journal of Organic Chemistry·Chongwei ZhuRemi Chauvin
Jan 27, 2015·Chemical Communications : Chem Comm·Diego Rodríguez-LojoEnrique Guitián
Apr 1, 2016·Chemical Communications : Chem Comm·Iago PozoDolores Pérez
Aug 15, 2019·Chemistry : a European Journal·Takanori IwasakiNobuaki Kambe
May 5, 2011·Chemical Communications : Chem Comm·Chitoshi KitamuraHiroyoshi Naito
Nov 19, 2011·Angewandte Chemie·José M AlonsoEnrique Guitián
May 25, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Junbo LiQichun Zhang
Aug 29, 2019·Chemical Communications : Chem Comm·Christoph DohmenBrian O Patrick
Jan 17, 2020·ChemPlusChem·Shigeki MoriHidemitsu Uno
Feb 19, 2021·Chemical Reviews·Jiarong ShiYang Li
May 17, 2011·The Journal of Organic Chemistry·Takakazu KimotoKenji Kobayashi
Jan 31, 2019·Journal of the American Chemical Society·Jinlian WangQian Miao
Aug 29, 2017·The Journal of Organic Chemistry·Ning SunYuanhong Liu
Sep 14, 2017·Organic Letters·Youpeng LiZebing Zeng

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