The first regioregular head-to-tail poly(3-hexylthiophene-2,5-diyl) and a regiorandom isopolymer: Ni vs Pd catalysis of 2(5)-bromo-5(2)-(bromozincio)-3-hexylthiophene polymerization

Journal Article · Tue Dec 01 23:00:00 EST 1992 · Journal of the American Chemical Society; (United States)

DOI:https://doi.org/10.1021/ja00051a066· OSTI ID:6539344

Chen, Tianan; Rieke, R D ^[1]

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1. Univ. of Nebraska, Lincoln (United States)

Recent research on poly(alkylthiophenes) (PAT) has concentrated on the regularity and structure of the polymer chain of PAT. The 3-alkyl substituent in a thiophene ring can be incorporated into a polymer chain with two different regioregularities: head-to-tail (HT) and head-to-head (HH). Head-to-head linkages can cause defects in the polymer chain. The highest regioregularity reported to date for HT-PAT is 91% (usually 50-60% HT regioregularity). The authors report herein a new and facile synthesis which leads to the first completely head-to-tail regioregular poly(3-hexylthiophene 2,5-diyl) (HT-PHT) and an alternative synthesis which yields an unusual regiorandom PHT with almost equal distribution of different linkages in the polymer chain. Both polymers have been characterized by NMR, IR, elemental analysis, GPC (gel-permeation chromatography), and UV-vis. 11 refs., 2 figs., 1 tab.

• OSTI ID: 6539344
• Journal Information: Journal of the American Chemical Society; (United States), Journal Name: Journal of the American Chemical Society; (United States) Vol. 114:25; ISSN JACSAT; ISSN 0002-7863
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ABSORPTION SPECTROSCOPY
CATALYSIS
CATALYTIC EFFECTS
CHEMICAL COMPOSITION
CHEMICAL PREPARATION
CHEMICAL REACTIONS
CHROMATOGRAPHY
COMPLEXES
GEL PERMEATION CHROMATOGRAPHY
HETEROCYCLIC COMPOUNDS
MAGNETIC RESONANCE
MOLECULAR STRUCTURE
NICKEL COMPLEXES
NUCLEAR MAGNETIC RESONANCE
ORGANIC COMPOUNDS
ORGANIC SULFUR COMPOUNDS
PALLADIUM COMPLEXES
PHOSPHINES
PHOSPHORUS COMPOUNDS
POLYCYCLIC SULFUR HETEROCYCLES
POLYMERIZATION
RESONANCE
SEPARATION PROCESSES
SPECTROSCOPY
SYNTHESIS
TRANSITION ELEMENT COMPLEXES