Synthesis of photo- and ionochromic N-acylated 2-(aminomethylene)benzo[b]thiophene-3(2Н)-ones with a terminal phenanthroline group

• Vladimir P. Rybalkin,
• Sofiya Yu. Zmeeva,
• Lidiya L. Popova,
• Irina V. Dubonosova,
• Olga Yu. Karlutova,
• Oleg P. Demidov,
• Alexander D. Dubonosov and
• Vladimir A. Bren

Beilstein J. Org. Chem. 2024, 20, 552–560, doi:10.3762/bjoc.20.47

• inverse photochromism), such as merocyanine forms of spiropyrans and spirooxazines, azomethine imines, thioindigoid dyes and N→O acylotropic systems [12][13][14][15]. Recently, they have been actively used to create next-generation molecular switches, materials with new properties (in particular, color

Reversible intramolecular photocycloaddition of a bis(9-anthrylbutadienyl)paracyclophane – an inverse photochromic system. (Photoactive cyclophanes 5)

• Henning Hopf,
• Christian Beck,
• Jean-Pierre Desvergne,
• Henri Bouas-Laurent,
• Peter G. Jones and
• Ludger Ernst

Beilstein J. Org. Chem. 2009, 5, No. 20, doi:10.3762/bjoc.5.20

• recovered by irradiation at 306 nm or by heating. This ‘inverse’ photochromic system has a potential for optical information storage, compound 4 being stable in visible light, at ambient temperature. Keywords: anthracenes; cyclophanes; inverse photochromism; photocycloaddition; Introduction Photochromism

• established systems show a ‘positive’ photochromism in which the electronic absorption spectrum of the product P is red-shifted [1]. When the electronic absorption spectrum of P is blue-shifted, the photochromism is said to be ‘negative’ or ‘inverse’ [1]. Inverse photochromism is encountered in photoaddition

• of conjugated systems [10][11][12][13][14][15][16][17] and may be interesting for information storage materials because the photoproducts can be operated in visible light. Inverse photochromism was recently observed for some vinylogs of cinnamophanes [18][19], such as compound 1 (Figure 2). Several