Multiturn hollow helices: Synthesis and folding of long aromatic oligoamides

Yulong Zhong; Brice Kauffmann; Wenwu Xu; Zhong Lin Lu; Yann Ferrand; Ivan Huc; Xiao Cheng Zeng; Rui Liu; Bing Gong

doi:10.1021/acs.orglett.0c02481

Multiturn hollow helices: Synthesis and folding of long aromatic oligoamides

Yulong Zhong, Brice Kauffmann, Wenwu Xu, Zhong Lin Lu, Yann Ferrand, Ivan Huc, Xiao Cheng Zeng, Rui Liu, Bing Gong

Chemistry

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

4 Scopus citations

Abstract

Aromatic oligoamides adopting helical conformations are synthesized by coupling carboxyl-terminated basic units having two, four, and eight residues to amine-terminated oligomer precursors. Coupling yields show no noticeable reduction with the size of the basic units or the final product. One- and two-dimensional NMR spectroscopy and computational studies demonstrate the reliable helical folding of these oligomers. The X-ray structure of 16mer 7 reveals a compact, multiturn helix having a 9 Å inner pore.

Original language	English (US)
Pages (from-to)	6938-6942
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.0c02481
State	Published - Sep 4 2020

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Multiturn hollow helices: Synthesis and folding of long aromatic oligoamides",

abstract = "Aromatic oligoamides adopting helical conformations are synthesized by coupling carboxyl-terminated basic units having two, four, and eight residues to amine-terminated oligomer precursors. Coupling yields show no noticeable reduction with the size of the basic units or the final product. One- and two-dimensional NMR spectroscopy and computational studies demonstrate the reliable helical folding of these oligomers. The X-ray structure of 16mer 7 reveals a compact, multiturn helix having a 9 {\AA} inner pore.",

author = "Yulong Zhong and Brice Kauffmann and Wenwu Xu and Lu, {Zhong Lin} and Yann Ferrand and Ivan Huc and Zeng, {Xiao Cheng} and Rui Liu and Bing Gong",

note = "Funding Information: This work was supported by the National Science Foundation (Grant CHE-1905094 to B.G. and X.C.Z.). Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

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doi = "10.1021/acs.orglett.0c02481",

language = "English (US)",

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T1 - Multiturn hollow helices

T2 - Synthesis and folding of long aromatic oligoamides

AU - Zhong, Yulong

AU - Kauffmann, Brice

AU - Xu, Wenwu

AU - Lu, Zhong Lin

AU - Ferrand, Yann

AU - Huc, Ivan

AU - Zeng, Xiao Cheng

AU - Liu, Rui

AU - Gong, Bing

PY - 2020/9/4

Y1 - 2020/9/4

N2 - Aromatic oligoamides adopting helical conformations are synthesized by coupling carboxyl-terminated basic units having two, four, and eight residues to amine-terminated oligomer precursors. Coupling yields show no noticeable reduction with the size of the basic units or the final product. One- and two-dimensional NMR spectroscopy and computational studies demonstrate the reliable helical folding of these oligomers. The X-ray structure of 16mer 7 reveals a compact, multiturn helix having a 9 Å inner pore.

AB - Aromatic oligoamides adopting helical conformations are synthesized by coupling carboxyl-terminated basic units having two, four, and eight residues to amine-terminated oligomer precursors. Coupling yields show no noticeable reduction with the size of the basic units or the final product. One- and two-dimensional NMR spectroscopy and computational studies demonstrate the reliable helical folding of these oligomers. The X-ray structure of 16mer 7 reveals a compact, multiturn helix having a 9 Å inner pore.

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JO - Organic Letters

JF - Organic Letters

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ER -

Multiturn hollow helices: Synthesis and folding of long aromatic oligoamides

Abstract

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