Chiroptical properties of homopolymers and block copolymers synthesized from the enantiomeric monomers N-acryloyl-L-alanine and N-acryloyl-D-alanine using aqueous RAFT polymerization

Brad S. Lokitz; Jonathan E. Stempka; Adam W. York; Yuting Li; Hitesh K. Goel; G. Reid Bishop; Charles L. McCormick

doi:10.1071/CH06264

Chiroptical properties of homopolymers and block copolymers synthesized from the enantiomeric monomers N-acryloyl-L-alanine and N-acryloyl-D-alanine using aqueous RAFT polymerization

Brad S. Lokitz, Jonathan E. Stempka, Adam W. York, Yuting Li, Hitesh K. Goel, G. Reid Bishop, Charles L. McCormick

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

35 Scopus citations

Abstract

Chiral homo- and block copolymers based on the enantiomeric monomers N-acryloyl-l-alanine (ALAL) and N-acryloyl-d-alanine (ADAL) were prepared directly in water using controlled reversible addition?fragmentation chain transfer (RAFT) polymerization. The polymerization of the chiral monomers proceeded in a controlled fashion producing the respective homopolymers, block copolymers, and a statistical copolymer with targeted molecular weights and narrow molecular weight distributions. The chiroptical activity of these biomimetic polymers and their analogous model compounds was investigated using circular dichroism (CD). P(ALAL) and P(ADAL) were shown to be optically active exhibiting mirror image CD spectra. In addition, statistical and enantiomeric block copolymers prepared at 1:1 stochiometric ratios exhibited virtually no optical activity.

Original language	English
Pages (from-to)	749-754
Number of pages	6
Journal	Australian Journal of Chemistry
Volume	59
Issue number	10
DOIs	https://doi.org/10.1071/CH06264
State	Published - 2006
Externally published	Yes

Funding

We gratefully acknowledge The Department of Energy (DE-FC26-01BC15317), Genzyme, MRSEC program of the National Science Foundation (DR-0213883), and the Robert M. Hearin Foundation as well as Mississippi College and the W. M. Keck Foundation for financial support. We would also like to thank Wako Chemicals for donating V-501.

Funders	Funder number
Mississippi College
Robert M. Hearin Foundation
National Science Foundation	DR-0213883
U.S. Department of Energy	DE-FC26-01BC15317
W. M. Keck Foundation
Genzyme
Materials Research Science and Engineering Center, Harvard University

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Lokitz, B. S., Stempka, J. E., York, A. W., Li, Y., Goel, H. K., Bishop, G. R., & McCormick, C. L. (2006). Chiroptical properties of homopolymers and block copolymers synthesized from the enantiomeric monomers N-acryloyl-L-alanine and N-acryloyl-D-alanine using aqueous RAFT polymerization. Australian Journal of Chemistry, 59(10), 749-754. https://doi.org/10.1071/CH06264

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title = "Chiroptical properties of homopolymers and block copolymers synthesized from the enantiomeric monomers N-acryloyl-L-alanine and N-acryloyl-D-alanine using aqueous RAFT polymerization",

abstract = "Chiral homo- and block copolymers based on the enantiomeric monomers N-acryloyl-l-alanine (ALAL) and N-acryloyl-d-alanine (ADAL) were prepared directly in water using controlled reversible addition?fragmentation chain transfer (RAFT) polymerization. The polymerization of the chiral monomers proceeded in a controlled fashion producing the respective homopolymers, block copolymers, and a statistical copolymer with targeted molecular weights and narrow molecular weight distributions. The chiroptical activity of these biomimetic polymers and their analogous model compounds was investigated using circular dichroism (CD). P(ALAL) and P(ADAL) were shown to be optically active exhibiting mirror image CD spectra. In addition, statistical and enantiomeric block copolymers prepared at 1:1 stochiometric ratios exhibited virtually no optical activity.",

author = "Lokitz, {Brad S.} and Stempka, {Jonathan E.} and York, {Adam W.} and Yuting Li and Goel, {Hitesh K.} and Bishop, {G. Reid} and McCormick, {Charles L.}",

year = "2006",

doi = "10.1071/CH06264",

language = "English",

volume = "59",

pages = "749--754",

journal = "Australian Journal of Chemistry",

issn = "0004-9425",

publisher = "CSIRO Publishing",

number = "10",

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Chiroptical properties of homopolymers and block copolymers synthesized from the enantiomeric monomers N-acryloyl-L-alanine and N-acryloyl-D-alanine using aqueous RAFT polymerization. / Lokitz, Brad S.; Stempka, Jonathan E.; York, Adam W. et al.
In: Australian Journal of Chemistry, Vol. 59, No. 10, 2006, p. 749-754.

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

TY - JOUR

T1 - Chiroptical properties of homopolymers and block copolymers synthesized from the enantiomeric monomers N-acryloyl-L-alanine and N-acryloyl-D-alanine using aqueous RAFT polymerization

AU - Lokitz, Brad S.

AU - Stempka, Jonathan E.

AU - York, Adam W.

AU - Li, Yuting

AU - Goel, Hitesh K.

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AU - McCormick, Charles L.

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AB - Chiral homo- and block copolymers based on the enantiomeric monomers N-acryloyl-l-alanine (ALAL) and N-acryloyl-d-alanine (ADAL) were prepared directly in water using controlled reversible addition?fragmentation chain transfer (RAFT) polymerization. The polymerization of the chiral monomers proceeded in a controlled fashion producing the respective homopolymers, block copolymers, and a statistical copolymer with targeted molecular weights and narrow molecular weight distributions. The chiroptical activity of these biomimetic polymers and their analogous model compounds was investigated using circular dichroism (CD). P(ALAL) and P(ADAL) were shown to be optically active exhibiting mirror image CD spectra. In addition, statistical and enantiomeric block copolymers prepared at 1:1 stochiometric ratios exhibited virtually no optical activity.

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Chiroptical properties of homopolymers and block copolymers synthesized from the enantiomeric monomers N-acryloyl-L-alanine and N-acryloyl-D-alanine using aqueous RAFT polymerization

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