Exerting control over the helical chirality in the main chain of sergeants-and-soldiers-type poly(quinoxaline-2,3-diyl)s by changing from random to block copolymerization protocols

Journal of the American Chemical Society
Yuuya NagataMichinori Suginome

Abstract

Chiral random poly(quinoxaline-2,3-diyl) polymers of the sergeants-and-soldiers-type (sergeant units bearing (S)-3-octyloxymethyl groups) adopt an M- or P-helical conformation in the presence of achiral units bearing propoxymethyl or butoxy groups (soldier units), respectively. Unusual bidirectional induction of the helical sense can be observed for a copolymer with butoxy soldier units upon changing the mole fraction of the sergeant units. In the presence of 16-20% of sergeant units, the selective induction of a P-helix was observed, while the selective induction of an M-helix was observed for a mole fraction of sergeant units of more than 60%. This phenomenon could be successfully employed to control the helical chirality of copolymers by applying either random or block copolymerization protocols. Random or block copolymerization of sergeant and soldier monomers in a 18:82 ratio resulted in the formation of 250mers with almost absolute P- or M-helical conformation, respectively (>99% ee). Incorporation of a small amount of coordination sites into the random and block copolymers resulted in chiral macromolecular ligands, which allowed the enantioselective synthesis of both enantiomers in the Pd-catalyzed asymmetric hydrosilyla...Continue Reading

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Citations

Mar 22, 2016·Journal of the American Chemical Society·Alaric DesmarchelierLaurent Bouteiller
Nov 10, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Katsuhiro MaedaShigeyoshi Kanoh
Mar 17, 2017·Chemistry, an Asian Journal·Jijun YanLianxun Gao
Sep 4, 2015·Organic & Biomolecular Chemistry·Mohit KumarSubi J George
Dec 14, 2018·ChemistryOpen·Sandeep Kumar DeySheshanath V Bhosale
Jan 23, 2018·Chemical Communications : Chem Comm·Kazuto TakaishiTadashi Ema
Aug 14, 2019·Journal of the American Chemical Society·Yuya WadaTomoyuki Ikai
Dec 15, 2017·Journal of the American Chemical Society·Sandra AriasFélix Freire
Jun 14, 2019·The Journal of Physical Chemistry. B·Timur I BurganovXavier Assfeld
Nov 11, 2020·Journal of the American Chemical Society·Nathan J Van ZeeE W Meijer
Aug 30, 2018·Journal of the American Chemical Society·Katherine CobosFélix Freire

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