Journal of Chemical Software
Online ISSN : 1883-8359
Print ISSN : 0918-0761
ISSN-L : 0918-0761
Photochromism and Structural Chemistry of Benzo [1, 2, 3-kl : 4, 5, 6-k'l'] dixanthene and its analogues
Sumio TOKITAHitoshi NAITO
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1994 Volume 2 Issue 1 Pages 25-33

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Abstract

Benzo [1, 2, 3-kl : 4, 5, 6-k'l']dixanthene (1a) and its endoperoxide (2a) are well known as thermally stable photochromic compounds. Authors have already reported the synthesis and photochromic properties of sulfur analogue of (1a), benzo [1, 2, 3-kl : 4, 5, 6-k'l'] bisthioxanthene (1b), and its endoperoxide (2b). Relative rate for thermolysis of (2b) to give (1b) in refluxing xylcne compared with that of (2a) to give (1a) was 0.03. This result will be explained on the heats of formation or the molecular geometries of (1a) and (1b) in terms of dihedral angles between planes of xanthene (or thioxanthene) rings as revealed by PM3 full geometry optimization method.S

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