ORGANIC
LETTERS
2003
Vol. 5, No. 9
1435-1437
Synthesis and Photochromic Properties
of Functional Diarylethene with a
2,5-Dihydrothiophene Bridging Unit
Yi Chen,* De X. Zeng, and Mei G. Fan
Technical Institute of Physics and Chemistry, The Chinese Academy of Sciences,
Beijing, 100101, P. R. China
Received January 30, 2003
ABSTRACT
A novel synthetic route to symmetric and nonsymmetric dithienylethene derivatives with a 2,5-dihydrothiophene bridging unit was described.
A class of new functional photochromic compounds was prepared and showed photochromic properties similar to those of known diarylethenes.
Diarylethenes, notably the bis(thien-3-yl) system, display
excellent photochromic properties1 and are the most promis-
ing photochromic compounds among various photochromic
compounds for photoelectronic applications such as optical
memony media2 and photoswitching devices3 because of their
fatigue resistant4 and thermally irreversible properties.5 There
are several 1,2-bis(thien-3-yl) systems containing maleic
anhydride,6 maleimide,7 perfluorocyclopentene,8 and cyclo-
pentene9 units that have been employed so far. Each unit
has its advantages and disadvantages. Diarylethenes with a
perfluorocyclopentene bridging unit, for instance, exhibit
excellent photochromic properties. However, the expensive
and rather volatile starting material octafluorocyclopentene
is a major disadvantage. Both diarylmaleic anhydrides and
diarylmaleimides are readily accessible but are sensitive to
acidic conditions.
We report herein a new class of diarylethenes with a 2,5-
dihydrothiphene unit10 and a novel synthetic route to prepar-
ing symmetric and nonsymmetric functional dithienylethene
derivatives. We also present the photochromic properties of
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10.1021/ol034166r CCC: $25.00 © 2003 American Chemical Society
Published on Web 03/29/2003