Beilstein J. Org. Chem.2019,15, 2161–2169, doi:10.3762/bjoc.15.213
electron-withdrawing cyano groups than when they are electron-donating methoxy groups.
Keywords: aromaticstabilizationenergy; diarylethene; ruthenium(I) catalysed Huisgen cyclization; terarylene; thermally reversible photochromism; Introduction
Diarylethenes are one of the most widely investigated
among the photochromic families [1][2][3]. They are known to show thermally irreversible photochromism. However, some of them are thermally reversible [4]: (1) when the aromaticstabilizationenergy of the aromatic rings is large [5]; (2) when the substituent groups on the ring-closing carbon atoms are
related families of diarylethenes, are largely thermally reversible [10][12] although some are irreversible when the aromaticstabilizationenergy of the aromatic rings is small [11]. Their syntheses are usually carried out by the sequential construction of the central aromatic ring at the final stage [10
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Graphical Abstract
Scheme 1:
Reaction mechanisms of Huisgen cyclization catalyzed by Cu(I) and Ru(I).