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Metal‐induced supramolecular chirality in optically active polymers of oxazoline‐substituted N ‐phenylmaleimides
Author(s) -
Xi Xiujuan,
Jiang Liming,
Sun Weilin,
Shen Zhiquan
Publication year - 2007
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20369
Subject(s) - chemistry , chirality (physics) , oxazoline , cotton effect , polymerization , circular dichroism , supramolecular chemistry , monomer , substituent , polymer chemistry , supramolecular chirality , chromophore , polymer , supramolecular polymers , crystallography , photochemistry , stereochemistry , organic chemistry , crystal structure , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark , catalysis
Polymerization of N ‐phenylmaleimide derivatives bearing a chiral oxazoline substituent at ortho ‐position on the phenyl group (namely, N ‐[ o‐ (4,5‐dihydro‐1,3‐oxazol‐2‐yl)phenyl]maleimides, OPMI) was carried out with diethylzinc (Et 2 Zn) as an initiator. The resulting polymers exhibited a quite high specific rotation and a unique split‐type circular dichroism. Furthermore, an induced Cotton effect was observed in the π–π* transition region of the chromophores upon complexation of these polymers with copper(II) salt in tetrahydrofuran solution, indicating the formation of chiral supramolecular aggregates. The induced supramolecular chirality was found to be dependent on the absolute configuration of monomer units, that is, the polymers with ( R )‐configurational oxazolinyl chromophores tended to form chiral aggregates with levorotatory handedness, while polymers obtained from the ( S )‐monomer offered dextrogyrate one upon the addition of Cu(II) salt. Chirality, 2007. © 2007 Wiley‐Liss, Inc.