2005
DOI: 10.1021/ol047768z
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Poly(thiaheterohelicene):  A Stiff Conjugated Helical Polymer Comprised of Fused Benzothiophene Rings

Abstract: A novel helical aromatic polymer comprised of fused benzothiophene rings, poly(thiaheterohelicene), was synthesized via an intramolecular ring-closing reaction with a controlled helicity to one-sided bias. The synthetic helicity control involved the induction of the helical conformation and its fixation. The ladder polymer showed both an extended pi-conjugation and planarity and a very stiff helical structure. [structure: see text]

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Cited by 74 publications
(43 citation statements)
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“…The design of nonbiological structures often relies on the molecular self-organization of superstructures [9] and focuses principally on applications in nanotechnology, optics, and electronics. [10][11][12] Among these systems, conjugated helical molecules composed of ortho-fused aromatic rings, called (homo-or hetero-) helicenes, have been extensively studied, both experimentally [13][14][15][16][17][18] and theoretically. [19][20][21] In particular, strategies have been proposed to enhance their secondorder NLO responses.…”
Section: Introductionmentioning
confidence: 99%
“…The design of nonbiological structures often relies on the molecular self-organization of superstructures [9] and focuses principally on applications in nanotechnology, optics, and electronics. [10][11][12] Among these systems, conjugated helical molecules composed of ortho-fused aromatic rings, called (homo-or hetero-) helicenes, have been extensively studied, both experimentally [13][14][15][16][17][18] and theoretically. [19][20][21] In particular, strategies have been proposed to enhance their secondorder NLO responses.…”
Section: Introductionmentioning
confidence: 99%
“…The broader context of the former work is to be seen in an attempt to create model structures for graphene [124]. A two-step approach was also applied to an m-phenylene precursor to obtain a helicene-type structure by Nishide et al [125].…”
Section: Miscellaneousmentioning
confidence: 99%
“…The compounds belonging to the general class of oxa-helicenes and thia-helicenes have been synthesized, and their various properties have been studied [38][39][40][41][42][43][44][45]. Recently Sundar and Bedekar [46] reported the design and synthesis of oxygen-containing 7,12,17-trioxa [11] helicene.…”
Section: Introductionmentioning
confidence: 99%