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A novel synthesis of polymers with anthracene and dihydroanthracene subunits in the main chain
Author(s) -
Bartz Thomas,
Klapper Markus,
Müllen Klaus,
Schulz Rolf C.
Publication year - 1993
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.4990310206
Subject(s) - anthracene , moiety , alkylation , deprotonation , aromatization , polymer , butyllithium , chemistry , polymer chemistry , condensation polymer , side chain , chain (unit) , organic chemistry , catalysis , ion , physics , astronomy
A new polycondensation method to connect redox‐active and chromophoric subunits by forming a C‐C bond and leading to a polyhydrocarbon is described. 1,ω‐bis(9,10‐Dihydro‐9‐anthry)alkanes with various alkylene spacers can be deprotonated by butyllithium to afford a monoanion in each dihydroanthracene moiety. Alkylation with dielectrophiles such as dibromoalkanes yields soluble polymers with dihydroanthracene units in the main chain. The reaction proceeds regioselectively in the 9,10‐position. Aromatization generates a polymer with anthracene units. The molecular weights are determined by GPC up to M̄ n = 10 000. To prove the structure and to calibrate the GPC, suitable model compounds were synthesized.