Guest-Induced Arylamide Polymer Helicity: Twist-Sense Bias and Solvent-Dependent Helicity Inversion

Peng Zhang; Liang Zhang; Ze Kun Wang; Yun Chang Zhang; Rong Guo; Hui Wang; Dan Wei Zhang; Zhan Ting Li

doi:10.1002/asia.201600289

Guest-Induced Arylamide Polymer Helicity: Twist-Sense Bias and Solvent-Dependent Helicity Inversion

Peng Zhang
, Liang Zhang
, Ze Kun Wang
, Yun Chang Zhang
, Rong Guo
, Hui Wang^*
, Dan Wei Zhang
, Zhan Ting Li

^*Corresponding author for this work

Fudan University

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

A benzene/naphthalene alternately incorporated amide polymer was synthesized and characterized. ¹H NMR spectroscopy, fluorescence, and circular dichroism (CD) experiments indicated that, in chloroform, the polymer could be induced by the chiral l-aspartic acid dianion or one of its derivatives to form a helical tubular conformation with twist-sense bias. CD titration studies showed that the l-aspartic acid dianion (8 equiv.) could lead to a maximum Cotton effect. It was also revealed that the twist-sense bias obeyed the majority rule, and 70 % enantiomeric excess could realize the maximum helicity bias. Adding acetonitrile to the solution of chloroform caused inversion of the guest-induced helicity bias of the polymer.

Original language	English
Pages (from-to)	1725-1730
Number of pages	6
Journal	Chemistry - An Asian Journal
Volume	11
Issue number	11
DOIs	https://doi.org/10.1002/asia.201600289
State	Published - 6 Jun 2016
Externally published	Yes

Keywords

foldamers
guest induction
helical structures
hydrogen bonds
polymers

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10.1002/asia.201600289

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@article{d6b3eb16ddbd4393955719d804c4186f,

title = "Guest-Induced Arylamide Polymer Helicity: Twist-Sense Bias and Solvent-Dependent Helicity Inversion",

abstract = "A benzene/naphthalene alternately incorporated amide polymer was synthesized and characterized. 1H NMR spectroscopy, fluorescence, and circular dichroism (CD) experiments indicated that, in chloroform, the polymer could be induced by the chiral l-aspartic acid dianion or one of its derivatives to form a helical tubular conformation with twist-sense bias. CD titration studies showed that the l-aspartic acid dianion (8 equiv.) could lead to a maximum Cotton effect. It was also revealed that the twist-sense bias obeyed the majority rule, and 70 \% enantiomeric excess could realize the maximum helicity bias. Adding acetonitrile to the solution of chloroform caused inversion of the guest-induced helicity bias of the polymer.",

keywords = "foldamers, guest induction, helical structures, hydrogen bonds, polymers",

author = "Peng Zhang and Liang Zhang and Wang, \{Ze Kun\} and Zhang, \{Yun Chang\} and Rong Guo and Hui Wang and Zhang, \{Dan Wei\} and Li, \{Zhan Ting\}",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2016",

month = jun,

day = "6",

doi = "10.1002/asia.201600289",

language = "英语",

volume = "11",

pages = "1725--1730",

journal = "Chemistry - An Asian Journal",

issn = "1861-4728",

publisher = "John Wiley and Sons Ltd",

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}

TY - JOUR

T1 - Guest-Induced Arylamide Polymer Helicity

T2 - Twist-Sense Bias and Solvent-Dependent Helicity Inversion

AU - Zhang, Peng

AU - Zhang, Liang

AU - Wang, Ze Kun

AU - Zhang, Yun Chang

AU - Guo, Rong

AU - Wang, Hui

AU - Zhang, Dan Wei

AU - Li, Zhan Ting

PY - 2016/6/6

Y1 - 2016/6/6

N2 - A benzene/naphthalene alternately incorporated amide polymer was synthesized and characterized. 1H NMR spectroscopy, fluorescence, and circular dichroism (CD) experiments indicated that, in chloroform, the polymer could be induced by the chiral l-aspartic acid dianion or one of its derivatives to form a helical tubular conformation with twist-sense bias. CD titration studies showed that the l-aspartic acid dianion (8 equiv.) could lead to a maximum Cotton effect. It was also revealed that the twist-sense bias obeyed the majority rule, and 70 % enantiomeric excess could realize the maximum helicity bias. Adding acetonitrile to the solution of chloroform caused inversion of the guest-induced helicity bias of the polymer.

AB - A benzene/naphthalene alternately incorporated amide polymer was synthesized and characterized. 1H NMR spectroscopy, fluorescence, and circular dichroism (CD) experiments indicated that, in chloroform, the polymer could be induced by the chiral l-aspartic acid dianion or one of its derivatives to form a helical tubular conformation with twist-sense bias. CD titration studies showed that the l-aspartic acid dianion (8 equiv.) could lead to a maximum Cotton effect. It was also revealed that the twist-sense bias obeyed the majority rule, and 70 % enantiomeric excess could realize the maximum helicity bias. Adding acetonitrile to the solution of chloroform caused inversion of the guest-induced helicity bias of the polymer.

KW - foldamers

KW - guest induction

KW - helical structures

KW - hydrogen bonds

KW - polymers

UR - https://www.scopus.com/pages/publications/84973402163

U2 - 10.1002/asia.201600289

DO - 10.1002/asia.201600289

M3 - 文章

AN - SCOPUS:84973402163

SN - 1861-4728

VL - 11

SP - 1725

EP - 1730

JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

IS - 11

ER -

Guest-Induced Arylamide Polymer Helicity: Twist-Sense Bias and Solvent-Dependent Helicity Inversion

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Keywords

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