Multiresponsive Chiroptical Switch of an Azobenzene-Containing Lipid: Solvent, Temperature, and Photoregulated Supramolecular Chirality

被引:126
作者
Duan, Pengfei [1 ]
Li, Yuangang [2 ]
Li, Liangchun [3 ,4 ]
Deng, Jingen [3 ,4 ]
Liu, Minghua [1 ]
机构
[1] Chinese Acad Sci, BNLMS, Key Lab Colloid, Inst Chem, Beijing 100190, Peoples R China
[2] Xian Univ Sci & Technol, Coll Chem & Chem Engn, Xian 710054, Peoples R China
[3] Chinese Acad Sci, Natl Engn Res Ctr Chiral Drugs, Chengdu 610041, Peoples R China
[4] Chinese Acad Sci, Key Lab Asymmetr Synth, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
基金
中国国家自然科学基金;
关键词
GEL-SOL TRANSITION; DENSITY FUNCTIONALS; MOLECULES; THERMOCHEMISTRY; AMPLIFICATION; HELICITY; GELATORS; GELATION; PROTEIN; DESIGN;
D O I
10.1021/jp110636b
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
An azobenzene-containing lipid was designed as a functional organogelator, and its self-assembly as well as the chiroptical properties were investigated. The gelator shows good gelation ability in various organic solvents ranging from polar to nonpolar solvents. Although the molecule did not show a CD signal in the absorption band of azobenzene in solution, supramolecular chirality was observed upon gel formation. Moreover, the supramolecular chirality exhibited a multire-sponse to temperature, photoirradiation, and the solvent polarity. Particularly, positive supramolecular chirality was observed in polar solvents, while it inverted to a negative one in nonpolar solvents. All the responses in relating to the supramolecular chirality were reversible and thus produced a multiresponsive chiroptical switch.
引用
收藏
页码:3322 / 3329
页数:8
相关论文
共 49 条
[1]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652
[2]   Chiral architectures from macromolecular building blocks [J].
Cornelissen, JJLM ;
Rowan, AE ;
Nolte, RJM ;
Sommerdijk, NAJM .
CHEMICAL REVIEWS, 2001, 101 (12) :4039-4070
[3]   Tuning the Helicity of Self-Assembled Structure of a Sugar-Based Organogelator by the Proper Choice of Cooling Rate [J].
Cui, Jiaxi ;
Liu, Anhua ;
Guan, Yan ;
Zheng, Jia ;
Shen, Zhihao ;
Wan, Xinhua .
LANGMUIR, 2010, 26 (05) :3615-3622
[4]   Transcription of Chirality in the Organogel Systems Dictates the Enantiodifferentiating Photodimerization of Substituted Anthracene [J].
Dawn, Arnab ;
Shiraki, Tomohiro ;
Haraguchi, Shuichi ;
Sato, Hiroki ;
Sada, Kazuki ;
Shinkai, Seiji .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (12) :3676-3689
[5]   Spectroscopic properties and gelling ability of a set of rod-like 2,3-disubstituted anthracenes [J].
Desvergne, JP ;
Brotin, T ;
Meerschaut, D ;
Clavier, G ;
Placin, F ;
Pozzo, JL ;
Bouas-Laurent, H .
NEW JOURNAL OF CHEMISTRY, 2004, 28 (02) :234-243
[6]   Water gelation by small organic molecules [J].
Estroff, LA ;
Hamilton, AD .
CHEMICAL REVIEWS, 2004, 104 (03) :1201-1217
[7]   Chiroptical molecular switches [J].
Feringa, BL ;
van Delden, RA ;
Koumura, N ;
Geertsema, EM .
CHEMICAL REVIEWS, 2000, 100 (05) :1789-1816
[8]   In control of motion: From molecular switches to molecular motors [J].
Feringa, BL .
ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (06) :504-513
[9]  
Feringa BL, 1999, ANGEW CHEM INT EDIT, V38, P3419
[10]   RECONSTITUTION OF ACTIVE TOBACCO MOSAIC VIRUS FROM ITS INACTIVE PROTEIN AND NUCLEIC ACID COMPONENTS [J].
FRAENKELCONRAT, H ;
WILLIAMS, RC .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1955, 41 (10) :690-698