Fluorescent Dendritic Organogels Based on 2-(2′-Hydroxyphenyl)benzoxazole: Emission Enhancement and Multiple Stimuli-Responsive Properties

被引:63
作者
Chen, Hui [1 ,2 ,3 ]
Feng, Yu [2 ]
Deng, Guo-Jun [1 ,3 ]
Liu, Zhi-Xiong [2 ,3 ]
He, Yan-Mei [2 ,3 ]
Fan, Qing-Hua [2 ,3 ]
机构
[1] Xiangtan Univ, Key Lab Environm Friendly Chem & Applicat, Minist Educ, Coll Chem, Xiangtan 411105, Peoples R China
[2] Chinese Acad Sci, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
[3] Chinese Acad Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China
基金
中国国家自然科学基金;
关键词
aggregation; dendrimers; fluorescence; multiresponsiveness; sol-gel processes; supramolecular chemistry; INTRAMOLECULAR PROTON-TRANSFER; POLY(BENZYL ETHER) DENDRONS; SUPRAMOLECULAR GELS; TRANSFER ESIPT; HIGHLY EFFICIENT; GELATION; MULTISTIMULI; GELATORS; TRANSITION; DESIGN;
D O I
10.1002/chem.201500849
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new highly efficient and versatile poly(benzyl ether) dendritic organogelator HPB-G(1) with 2-(2'-hydroxyphenyl) benzoxazole (HPB) at the focal point has been designed and synthesized. HPB-G(1) can form stable organogels toward various apolar and polar organic solvents. Further studies revealed that intermolecular multiple pi-pi stacking interactions are the main driving forces for the formation of the organogels. Notably, dendron HPB-G(1) exhibited a significantly enhanced emission in the gel state in contrast to weak emission in solution. Most interestingly, these dendritic organogels exhibited multiple stimuli-responsive behaviors upon exposure to environmental stimuli, including temperature, sonication, shear stress, and the presence of anions, metal cations, acids/ bases, thus leading to reversible sol-gel phase transitions.
引用
收藏
页码:11018 / 11028
页数:11
相关论文
共 110 条
[31]   Chemically reversible organogels: Aliphatic amines as "latent" gelators with carbon dioxide [J].
George, M ;
Weiss, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (42) :10393-10394
[32]   Excited state intramolecular proton transfer and metal ion complexation of 2-(2′-hydroxyphenyl)benzazoles in aqueous solution [J].
Henary, MM ;
Fahrni, CJ .
JOURNAL OF PHYSICAL CHEMISTRY A, 2002, 106 (21) :5210-5220
[33]   Zinc(II)-selective ratiometric fluorescent sensors based on inhibition of excited-state intramolecular proton transfer [J].
Henary, MM ;
Wu, YG ;
Fahrni, CJ .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (12) :3015-3025
[34]  
Hirst A. R., 2008, ANGEW CHEM, V120, P8122
[35]   High-Tech Applications of Self-Assembling Supramolecular Nanostructured Gel-Phase Materials: From Regenerative Medicine to Electronic Devices [J].
Hirst, Andrew R. ;
Escuder, Beatriu ;
Miravet, Juan F. ;
Smith, David K. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (42) :8002-8018
[36]   Dendritic gelators [J].
Hirst, AR ;
Smith, DK .
LOW MOLECULAR MASS GELATORS: DESIGN, SELF-ASSEMBLY, FUNCTION, 2005, 256 :237-273
[37]   Aggregation-induced emission: phenomenon, mechanism and applications [J].
Hong, Yuning ;
Lam, Jacky W. Y. ;
Tang, Ben Zhong .
CHEMICAL COMMUNICATIONS, 2009, (29) :4332-4353
[38]   Recent Experimental Advances on Excited-State Intramolecular Proton Coupled Electron Transfer Reaction [J].
Hsieh, Cheng-Chih ;
Jiang, Chang-Ming ;
Chou, Pi-Tai .
ACCOUNTS OF CHEMICAL RESEARCH, 2010, 43 (10) :1364-1374
[39]   A highly efficient, preorganized macrobicyclic receptor for halides based on CH••• and NH••• anion interactions [J].
Ilioudis, CA ;
Tocher, DA ;
Steed, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (39) :12395-12402
[40]   Dye-based organogels: Stimuli-responsive soft materials based on one-dimensional self-assembling aromatic dyes [J].
Ishi-i, T ;
Shinkai, S .
SUPERMOLECULAR DYE CHEMISTRY, 2005, 258 :119-160