Synthesis of Some New Functionalized 2,4,4,6-Tetraphenyl-4H-thiopyrans and Study on Their Photocolouration

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Title:Synthesis of Some New Functionalized 2,4,4,6-Tetraphenyl-4H-thiopyrans and Study on Their Photocolouration
Creators:
Kroulík, Jiří
Chadim, Martin
Polášek, Miroslav
Nešpůrek, Stanislav
Kuthan, Josef
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 63, 5, pp. 662-680
Uncontrolled Keywords:Photochemistry, Photocolouration, Lithiodebromination, Photochromism, Cyanodebromination, Thiopyrans, Hypervalent structures

Abstract

A series of nineteen new 2,4,4,6-tetraphenyl-4<i>H</i>-thiopyrans both symmetrically and asymmetrically functionalized in the 3- and 5-positions of the 4<i>H</i>-thiopyran ring (-Br, -NO<sub>2</sub>, -CN) and/or in the 4-positions of the 2- and 6-phenyl groups (-Br, -CN, -OMe, -CO-Ph, -COCF<sub>3</sub>, -CO<sub>2</sub>H) was prepared and the influence of the substituents on their photocolouration was followed. The title compounds were prepared by substitution reactions of the parent thiopyrans or by cyclization of suitably substituted 1,3,3,5-tetraarylpentane-1,5-diones. The substances lacking the 3,5-substituents exhibited blue or green UV-photocolouration while the 3- and/or 5-substituted species did not. Typical bleaching process for a selected compound is analyzed in terms of dispersive first-order kinetics.

Title:Synthesis of Some New Functionalized 2,4,4,6-Tetraphenyl-4H-thiopyrans and Study on Their Photocolouration
Creators:
Kroulík, Jiří
Chadim, Martin
Polášek, Miroslav
Nešpůrek, Stanislav
Kuthan, Josef
Uncontrolled Keywords:Photochemistry, Photocolouration, Lithiodebromination, Photochromism, Cyanodebromination, Thiopyrans, Hypervalent structures
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:63
Number:5
Page Range:pp. 662-680
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19980662UNSPECIFIED
ID Code:1332
Item Type:Article
Deposited On:06 Feb 2009 17:08
Last Modified:06 Feb 2009 16:08

Citation

Kroulík, Jiří; Chadim, Martin; Polášek, Miroslav; Nešpůrek, Stanislav; Kuthan, Josef (1998) Synthesis of Some New Functionalized 2,4,4,6-Tetraphenyl-4H-thiopyrans and Study on Their Photocolouration. Collection of Czechoslovak Chemical Communications, 63 (5). pp. 662-680. ISSN 0010-0765

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