Switching of optical‐resolution selectivity through the Onsager's reaction field: Chiral recognition of  dl ‐amino acids by hydrophilic/hydrophobic chitosans | Zendy

Sayama Daisuke | Zendy; Hatanaka Masashi | Zendy; Miyasaka Makoto | Zendy

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Switching of optical‐resolution selectivity through the Onsager's reaction field: Chiral recognition of dl ‐amino acids by hydrophilic/hydrophobic chitosans

Author(s) -

Sayama Daisuke,

Hatanaka Masashi,

Miyasaka Makoto

Publication year - 2020

Publication title -

journal of applied polymer science

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.575

H-Index - 166

eISSN - 1097-4628

pISSN - 0021-8995

DOI - 10.1002/app.48317

Subject(s) - selectivity , chitosan , adsorption , resolution (logic) , permittivity , chemistry , polymer , materials science , polymer chemistry , chemical engineering , organic chemistry , combinatorial chemistry , dielectric , catalysis , optoelectronics , artificial intelligence , computer science , engineering

Unusual switching of optical‐resolution selectivity in chitosan resins is reported. While in hydrophilic chitosan resins, the l ‐form of amino acids are selectively adsorbed, and in hydrophobic chitosan resins, the d ‐form was preferred. We found that the adsorption selectivity of the amino acids in the optical‐resolution agents is controlled by the hydrophilicity/hydrophobicity or permittivity of the resins, through the Onsager's reaction field. This intriguing selectivity switching is supported by the polarized continuum model calculations. This method provides a promising strategy for switching of optical‐resolution preferences by controlling the permittivity of the resins. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2020 , 137 , 48317.

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