Conjugated polymers with main chain chirality. 2. Synthesis of optically active polyarylenes

Qiao Sheng Hu, Dilrukshi Vitharana, Gang-yu Liu, Vijay Jain, Lin Pu

Research output: Contribution to journalArticle

59 Scopus citations

Abstract

An optically active polyarylene, (R)-3, has been prepared from the palladium-catalyzed Suzuki cross-coupling of an optically active binaphthyl molecule, (R)-2,2′-bis(hexyloxy )-1.1′-binaphthyl-6,6′-diboronic acid, (R)-2, with 1,4-dibromobenzene. GPC analysis of (R)-3 shows MM = 41 000 and Mm = 20 000 (PDI = 2.0) The specific optical rotation of (R)-3 is [a]D = -289.4o (c = 0.5, THF). The UV spectrum of the polymer displays a strong absorption at λmax = 328 nm. Maximum emissions at 388 and 407 nm are observed in the fluorescence spectrum of (R)-3. The polymer emits strong blue light under a UV lamp. Another optically active polyarylene, (R)-4, was also obtained by the polymerization of (R)-2 with 4.4′-dibromobiphenyl. GPC analysis shows its molecular weight is MMf = 47 000 and Mm = 14 000 (PDI = 3.4). The specific optical rotation is [a]D = -275o = (c = 0.22, CH2Cl2), Polymers rac-3 and rac-4 were synthesized by the polymerization of the racemic monomer rac-2 with either 1,4-dibromobenzene or 4,4′-dibromobiphenyl- Atomic force microscopic study on the polymer films spin-coated on mica shows interesting surface morphology. Pits and pinholes are observed; however, none of the polymers has longrange order.

Original languageEnglish (US)
Pages (from-to)5075-5082
Number of pages8
JournalMacromolecules
Volume29
Issue number15
StatePublished - Jul 15 1996
Externally publishedYes

ASJC Scopus subject areas

  • Materials Chemistry

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