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D-,L-苯丙氨酸诱导非手性菁染料的手性组装
引用本文:曾力希,何裕建,戴志锋,王健,王彩旗,杨永刚. D-,L-苯丙氨酸诱导非手性菁染料的手性组装[J]. 中国科学B辑, 2009, 39(7): 620-628
作者姓名:曾力希  何裕建  戴志锋  王健  王彩旗  杨永刚
作者单位:① 中国科学院研究生院化学与化学工程学院, 北京 100049; ② 北京大学天然药物及仿生药物国家重点实验室, 北京 100191; ③ 苏州大学材料与化学化工学部有机合成重点实验室, 苏州 215123
基金项目:致谢 本工作得到国家自然科学基金(批准号:20571085,20604033,20877099)、北京大学天然药物及仿生药物国家重点实验室开放基金(批准号:20080208)、中国科学院研究生院人才引进基金(2007-2009年)、国家自然科学基金(批准号:BK2007047)和江苏省有机化学重点实验室基金资助,特此一并致谢.
摘    要:超分子手性与分子自组装是生命体中非常重要和有趣的现象.报道了D,L-苯丙氨酸等氨基酸在氯化钠溶液中通过非共价键相互作用诱导非手性菁染料(Pseudoisocyanine,PIC)J-聚集体超分子手性的形成.实验结果表明,诱导的手性菁染料PIC聚集体发色团在π-π^*跃迁区域产生了特征的镜像圆二色性,其圆二色信号和强度强烈地依赖于氨基酸的绝对构型、浓度、侧链基团和溶液温度.原子力显微镜照片清楚地表明,^聚集体由相互交联的纳米纤维组成,诱导的圆二色性可能来源于纤维状聚集体的宏观螺旋排列.

关 键 词:超分子手性  自组装  氨基酸  J-聚集体  圆二色性
收稿时间:2008-11-27
修稿时间:2009-01-24

Chiral assembly of achiral pseudoisocyanine with D- and L-phenylalanine
ZENG LiXi,HE YuJian,DAI ZhiFeng,WANG Jian,WANG CaiQi,YANG YongGang. Chiral assembly of achiral pseudoisocyanine with D- and L-phenylalanine[J]. Science in China(Series B), 2009, 39(7): 620-628
Authors:ZENG LiXi  HE YuJian  DAI ZhiFeng  WANG Jian  WANG CaiQi  YANG YongGang
Affiliation:1. College of Chemistry and Chemical Engineering, Graduate University of Chinese Academy of Sciences, Beijing 100049, China; 2. State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, China; 3. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow (Suzhou) University, Suzhou 215123, China)
Abstract:Supramolecular chirality and molecular self-assembly are important and interesting phenomenon in living and non-living systems. In this paper, supramolecular chirality of achiral pseudoisocyanine (PIC) J-aggregates was successfully induced by D-, L-phenylalanine (Phe) and other amino acids in NaCI solution. The chiral J-aggregates show a characteristic, induced circular dichroism (ICD) in visible region of J-band chromophore which depends on the absolute configuration, concentration and side groups of α-amino acids, as well as temperature. The atomic force microscopy images indicated that the J-aggregates exist in large bundles of entangled nanofibers, the observed ICD might result from the macroscopic helical arrangement of the assemblies.
Keywords:supramolecular chirality   self-assembly   amino acid   J-aggregates induced circular dichroism
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