Preparation of phthalocyanines with eight benzylchalcogeno substituents from 5,6-dibromo-4,7-diethylbenzo[1,2,3]trichalcogenoles

The Journal of Organic Chemistry
Takeshi KimuraTakeshi Akasaka

Abstract

Benzo[1,2,3]trichalcogenoles with two bromine atoms on the benzene ring, 5,6-dibromo-4,7-diethylbenzo[1,2,3]trichalcogenoles (1a) and (1b) (chalcogen: 1a = S; 1b = Se), were first prepared by treating 2,3,5,6-tetrabromo-1,4-diethylbenzene (TBDEB) with elemental sulfur or amorphous selenium in DBU at 140 degrees C (for 1a) and 100 degrees C (for 1b) for 24 h. The structures of 1a and 1b were verified by NMR spectroscopy, mass spectrometry, and elemental analysis. X-ray crystallographic analysis ultimately showed that the substitution reactions of TBDEB proceeded at the two adjacent bromine atoms. To apply 1a and 1b to construction of phthalocyanine derivatives with sulfur or selenium functional groups, 4,5-bis(benzylchalcogeno)-3,6-diethylphthalonitriles (5a) and (5b) as key intermediates were prepared by way of introduction of alkyl groups (2-cyanoethyl or 4-nitrophenethyl groups) on two chalcogen atoms, substitution of two bromine atoms with nitrile groups, and subsequent exchange of alkyl groups with benzyl groups. Compound 5a was treated with lithium in n-pentanol at 100 degrees C for 1 h to produce 2,3,9,10,16,17,23,24-octakis(benzylthio)-1,4,8,11,15,18,22,25-octaethylphthalocyanine (6a). A similar treatment of 5b in n-hexa...Continue Reading

References

Aug 31, 2002·Angewandte Chemie·Takamitsu FukudaWilliam S Durfee
Feb 22, 2003·Chemistry : a European Journal·Frieder MitzelRüdiger Faust
May 17, 1999·Angewandte Chemie·Klaus B SimonsenJan Becher

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