ISSN:
1434-193X
Keywords:
Crystal engineering
;
Diynes
;
Photochemistry
;
Solid-state chemistry
;
Polymers
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
-The 1,6-bis(2,5-dimethoxyphenyl)hexa-2,4-diynes 4a-c were obtained from the corresponding 2,5-dimethoxybenzenes 1 by bromination followed by a copper-catalyzed Grignard reaction with 3-bromoprop-1-yne. Catalyzed coupling of the resulting 3-(2,5-dimethoxyphenyl)prop-1-ynes 3 under Hay conditions gave the hexa-2,4-diynes 4a-c in good yields. The molecular structures of the diynes 4a and 4b were determined by X-ray diffraction analysis. In each crystal structure, an unusual 1,6-synperiplanar conformation of the hexa-2,4-diyne unit is observed, with the 1,6-diphenyl substituents arranged in a coplanar orientation. According to the crystal structure data obtained, irradiation of diynes 4a and 4b afforded the deeply-colored, highly-ordered polymers 5a and 5b under topochemical control. Oxidation of 4a and 4b with cerium(IV) ammonium nitrate gave the corresponding 1,6-bis(2,5-dimethoxyphenyl)hexa-2,4-diyne-1,6-diones 6a and 6b.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
