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Synthesis of π‐conjugated polymers via regioregular organometallic polymers 2. Transformation of titanacyclopentadiene‐ containing polymer into poly( p ‐phenylene) derivative
Author(s) -
Kino Tomoko,
Nishiyama Hiroki,
Tomita Ikuyoshi
Publication year - 2010
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1593
Subject(s) - polymer , chemistry , polymer chemistry , polystyrene , conjugated system , phenylene , polymerization , derivative (finance) , protonation , condensation polymer , chloroform , molar mass distribution , titanium , organic chemistry , ion , financial economics , economics
The transformation of a regioregular organometallic polymer possessing titanacyclopentadiene‐2,5‐diyl units into a poly( p ‐phenylene) derivative by means of a novel polymer reaction method is described. The organotitianium polymer was prepared by the polymerization of 1,4‐diethynyl‐2,5‐dioctyloxybenzene and a low‐valent titanium complex, generated in situ from titanium(IV) isopropoxide and isopropylmagnesium chloride, and was subjected to the reaction with 3‐bromo‐1‐propyne followed by the protonation. Consequently, a polymer consisting of the substituted phenylene‐1,4‐diyl units could be produced in a high yield, which is soluble in organic solvents such as chloroform. The number‐average molecular weight and the molecular weight distribution of the polymer were estimated as 4800 and 1.8, respectively (GPC, polystyrene). The UV–vis absorption spectrum of the polymer exhibited the absorption maximum (λ max ) at 329 nm, which was bathochromically shifted by 53 nm compared with that of a model compound, 1,4‐bis(2‐methoxyphenyl)‐2‐methylbenzene (λ max = 276 nm). Copyright © 2010 John Wiley & Sons, Ltd.