Hydrobenzoin-based rigid chiral polymer

Anna Bieging; Li Xin Liao; Dominic V. McGrath

doi:10.1002/chir.10070

Hydrobenzoin-based rigid chiral polymer

Anna Bieging, Li Xin Liao, Dominic V. McGrath

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

2 Scopus citations

Abstract

We prepared a rigid, chiral polymer (1) from optically active hydrobenzoin-based subunits. Nonracemic monomer units 6 and 8 were prepared by asymmetric dihydroxylation (AD) methodology and polymerization was carried out under Sonagashira coupling conditions. Polymer I was obtained in good yield with a molecular weight M_n = 5,100 (PDI = 2.3). Modeling suggests that polymer 1 could form a stable helical mainchain conformation in solution or the solid state. The chiroptical data of the polymer and a low-molecular weight model compound (9) are compared.

Original language	English (US)
Pages (from-to)	258-263
Number of pages	6
Journal	Chirality
Volume	14
Issue number	2-3
DOIs	https://doi.org/10.1002/chir.10070
State	Published - 2002

Keywords

Asymmetric dihydroxylation
Foldamer
Macromolecular asymmetry
Phenyl ethynylene
Polymer
Sonagashira coupling
Stilbene diol

ASJC Scopus subject areas

Drug Discovery
Analytical Chemistry
Spectroscopy
Catalysis
Pharmacology
Organic Chemistry

Access to Document

10.1002/chir.10070

Cite this

@article{3f4946924bba404cba22dade16448105,

title = "Hydrobenzoin-based rigid chiral polymer",

abstract = "We prepared a rigid, chiral polymer (1) from optically active hydrobenzoin-based subunits. Nonracemic monomer units 6 and 8 were prepared by asymmetric dihydroxylation (AD) methodology and polymerization was carried out under Sonagashira coupling conditions. Polymer I was obtained in good yield with a molecular weight Mn = 5,100 (PDI = 2.3). Modeling suggests that polymer 1 could form a stable helical mainchain conformation in solution or the solid state. The chiroptical data of the polymer and a low-molecular weight model compound (9) are compared.",

keywords = "Asymmetric dihydroxylation, Foldamer, Macromolecular asymmetry, Phenyl ethynylene, Polymer, Sonagashira coupling, Stilbene diol",

author = "Anna Bieging and Liao, {Li Xin} and McGrath, {Dominic V.}",

year = "2002",

doi = "10.1002/chir.10070",

language = "English (US)",

volume = "14",

pages = "258--263",

journal = "Chirality",

issn = "0899-0042",

publisher = "Wiley-Liss Inc.",

number = "2-3",

}

TY - JOUR

T1 - Hydrobenzoin-based rigid chiral polymer

AU - Bieging, Anna

AU - Liao, Li Xin

AU - McGrath, Dominic V.

PY - 2002

Y1 - 2002

N2 - We prepared a rigid, chiral polymer (1) from optically active hydrobenzoin-based subunits. Nonracemic monomer units 6 and 8 were prepared by asymmetric dihydroxylation (AD) methodology and polymerization was carried out under Sonagashira coupling conditions. Polymer I was obtained in good yield with a molecular weight Mn = 5,100 (PDI = 2.3). Modeling suggests that polymer 1 could form a stable helical mainchain conformation in solution or the solid state. The chiroptical data of the polymer and a low-molecular weight model compound (9) are compared.

AB - We prepared a rigid, chiral polymer (1) from optically active hydrobenzoin-based subunits. Nonracemic monomer units 6 and 8 were prepared by asymmetric dihydroxylation (AD) methodology and polymerization was carried out under Sonagashira coupling conditions. Polymer I was obtained in good yield with a molecular weight Mn = 5,100 (PDI = 2.3). Modeling suggests that polymer 1 could form a stable helical mainchain conformation in solution or the solid state. The chiroptical data of the polymer and a low-molecular weight model compound (9) are compared.

KW - Asymmetric dihydroxylation

KW - Foldamer

KW - Macromolecular asymmetry

KW - Phenyl ethynylene

KW - Polymer

KW - Sonagashira coupling

KW - Stilbene diol

UR - http://www.scopus.com/inward/record.url?scp=0036152024&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0036152024&partnerID=8YFLogxK

U2 - 10.1002/chir.10070

DO - 10.1002/chir.10070

M3 - Article

C2 - 11835572

AN - SCOPUS:0036152024

SN - 0899-0042

VL - 14

SP - 258

EP - 263

JO - Chirality

JF - Chirality

IS - 2-3

ER -

Hydrobenzoin-based rigid chiral polymer

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this