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Title: Homochiral coordination polymers constructed from aminocarboxylate derivates: Effect of bipyridine on the amidation reaction

Abstract

Using aminocarboxylate derivates (S)-N-(4-cyanobenzoic)-glutamic acid (denoted as cbg, 1a) and (S)-N-(4-nitrobenzoic)-glutamic acid (denoted as nbg, 1b) as chiral ligands, five new homochiral coordination polymers formulated as [Cu(cbg)(H{sub 2}O){sub 2}]{sub n} (3), [Cu(cbop){sub 2}(4,4 Prime -bipy)(H{sub 2}O)]{sub n} (4) (cbop=(S)-N-(4-cyanobenzoic)-5-oxoproline, 4,4 Prime -bipy=4,4 Prime -bipyridine), {l_brace}[Cu(nbop){sub 2}(4,4 Prime -bipy)]{center_dot}4H{sub 2}O{r_brace}{sub n} (5) (nbop=(S)-N-(4-nitrobenzoic)-5-oxoproline), {l_brace}[Cd(nbop){sub 2}(4,4 Prime -bipy)]{center_dot}2H{sub 2}O{r_brace}{sub n} (6), and [Ni(nbop){sub 2}(4,4 Prime -bipy)(H{sub 2}O){sub 2}]{sub n} (7) have been hydrothermally synthesized and structurally characterized. Single-crystal X-ray diffraction study reveals that the original chirality of aminocarboxylate derivates is maintained in all these complexes. Complexes 3, 4, and 7 are one-dimensional infinite chain coordination polymers, while complexes 5 and 6 possess two-dimensional network structures. In situ cyclization of 1a and 1b was taken place in the formation of complexes 4-7, which may be due to the competition of 4,4 Prime -bipyridine with chiral ligands during the coordination process. Preliminary optical behavior investigation indicates that ligands 1a, 1b, and complexes 6, 7 are nonlinear optical active. - Graphical abstract: Using aminocarboxylate derivates as chiral ligands, five new homochiral coordination polymers possessing second harmonic generation activities have been hydrothermally synthesized. Highlights: Black-Right-Pointing-Pointer Two new chiral aminocarboxylate derivates were firstly synthesized. Black-Right-Pointing-Pointer Five newmore » homochiral metal organic complexes were obtained hydrothermally based on these ligands. Black-Right-Pointing-Pointer Intramolecular amidation was taken place on the aminocarboxylate derivates during the formation of these complexes. Black-Right-Pointing-Pointer In situ amidation may be due to the impact of 4,4 Prime -bipyridine. Black-Right-Pointing-Pointer The homochiral complexes are nonlinear optical active.« less

Authors:
; ; ; ; ;  [1]
  1. State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002 (China)
Publication Date:
OSTI Identifier:
22131130
Resource Type:
Journal Article
Journal Name:
Journal of Solid State Chemistry
Additional Journal Information:
Journal Volume: 192; Other Information: Copyright (c) 2012 Elsevier Science B.V., Amsterdam, The Netherlands, All rights reserved.; Country of input: International Atomic Energy Agency (IAEA); Journal ID: ISSN 0022-4596
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; BIPYRIDINES; CHIRALITY; COMPLEXES; CYCLIZATION; GLUTAMIC ACID; HARMONIC GENERATION; HYDROTHERMAL SYNTHESIS; LIGANDS; MONOCRYSTALS; NONLINEAR PROBLEMS; ORGANOMETALLIC COMPOUNDS; POLYMERS; X-RAY DIFFRACTION

Citation Formats

Jianshan, Chen, Tianlu, Sheng, Shengmin, Hu, Shengchang, Xiang, Ruibiao, Fu, Qilong, Zhu, and Wu Xintao, E-mail: wxt@fjirsm.ac.cn. Homochiral coordination polymers constructed from aminocarboxylate derivates: Effect of bipyridine on the amidation reaction. United States: N. p., 2012. Web. doi:10.1016/J.JSSC.2012.04.025.
Jianshan, Chen, Tianlu, Sheng, Shengmin, Hu, Shengchang, Xiang, Ruibiao, Fu, Qilong, Zhu, & Wu Xintao, E-mail: wxt@fjirsm.ac.cn. Homochiral coordination polymers constructed from aminocarboxylate derivates: Effect of bipyridine on the amidation reaction. United States. doi:10.1016/J.JSSC.2012.04.025.
Jianshan, Chen, Tianlu, Sheng, Shengmin, Hu, Shengchang, Xiang, Ruibiao, Fu, Qilong, Zhu, and Wu Xintao, E-mail: wxt@fjirsm.ac.cn. Wed . "Homochiral coordination polymers constructed from aminocarboxylate derivates: Effect of bipyridine on the amidation reaction". United States. doi:10.1016/J.JSSC.2012.04.025.
@article{osti_22131130,
title = {Homochiral coordination polymers constructed from aminocarboxylate derivates: Effect of bipyridine on the amidation reaction},
author = {Jianshan, Chen and Tianlu, Sheng and Shengmin, Hu and Shengchang, Xiang and Ruibiao, Fu and Qilong, Zhu and Wu Xintao, E-mail: wxt@fjirsm.ac.cn},
abstractNote = {Using aminocarboxylate derivates (S)-N-(4-cyanobenzoic)-glutamic acid (denoted as cbg, 1a) and (S)-N-(4-nitrobenzoic)-glutamic acid (denoted as nbg, 1b) as chiral ligands, five new homochiral coordination polymers formulated as [Cu(cbg)(H{sub 2}O){sub 2}]{sub n} (3), [Cu(cbop){sub 2}(4,4 Prime -bipy)(H{sub 2}O)]{sub n} (4) (cbop=(S)-N-(4-cyanobenzoic)-5-oxoproline, 4,4 Prime -bipy=4,4 Prime -bipyridine), {l_brace}[Cu(nbop){sub 2}(4,4 Prime -bipy)]{center_dot}4H{sub 2}O{r_brace}{sub n} (5) (nbop=(S)-N-(4-nitrobenzoic)-5-oxoproline), {l_brace}[Cd(nbop){sub 2}(4,4 Prime -bipy)]{center_dot}2H{sub 2}O{r_brace}{sub n} (6), and [Ni(nbop){sub 2}(4,4 Prime -bipy)(H{sub 2}O){sub 2}]{sub n} (7) have been hydrothermally synthesized and structurally characterized. Single-crystal X-ray diffraction study reveals that the original chirality of aminocarboxylate derivates is maintained in all these complexes. Complexes 3, 4, and 7 are one-dimensional infinite chain coordination polymers, while complexes 5 and 6 possess two-dimensional network structures. In situ cyclization of 1a and 1b was taken place in the formation of complexes 4-7, which may be due to the competition of 4,4 Prime -bipyridine with chiral ligands during the coordination process. Preliminary optical behavior investigation indicates that ligands 1a, 1b, and complexes 6, 7 are nonlinear optical active. - Graphical abstract: Using aminocarboxylate derivates as chiral ligands, five new homochiral coordination polymers possessing second harmonic generation activities have been hydrothermally synthesized. Highlights: Black-Right-Pointing-Pointer Two new chiral aminocarboxylate derivates were firstly synthesized. Black-Right-Pointing-Pointer Five new homochiral metal organic complexes were obtained hydrothermally based on these ligands. Black-Right-Pointing-Pointer Intramolecular amidation was taken place on the aminocarboxylate derivates during the formation of these complexes. Black-Right-Pointing-Pointer In situ amidation may be due to the impact of 4,4 Prime -bipyridine. Black-Right-Pointing-Pointer The homochiral complexes are nonlinear optical active.},
doi = {10.1016/J.JSSC.2012.04.025},
journal = {Journal of Solid State Chemistry},
issn = {0022-4596},
number = ,
volume = 192,
place = {United States},
year = {2012},
month = {8}
}