Synthesis of Zwitterionic Water-Soluble Oligofluorenes with Good Light-Harvesting Ability

被引：17

作者：

Xing, Chengfen ^{[1
]}

Liu, Libing ^{[1
]}

Shi, Zhiqiang ^{[2
]}

Li, Yuliang ^{[1
]}

Wang, Shu ^{[1
]}

机构：

[1] Chinese Acad Sci, Beijing Natl Lab Mol Sci, Key Lab Organ Solids, Inst Chem, Beijing 100190, Peoples R China

[2] Shandong Normal Univ, Dept Chem, Jinan 250014, Shandong, Peoples R China

来源：

ADVANCED FUNCTIONAL MATERIALS | 2010年 / 20卷 / 13期

基金：

中国国家自然科学基金;

关键词：

CATIONIC CONJUGATED POLYMERS; OPTICAL-DETECTION; CHEMICAL SENSORS; DNA METHYLATION; ENERGY-TRANSFER; POLYELECTROLYTES; POLYTHIOPHENES; DENDRIMERS; OLIGOMERS; BEHAVIOR;

D O I：

10.1002/adfm.200902155

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new water-soluble zwitterionic oligofluorene bearing carboxylic acid and quaternary ammonium as pendant groups (OF-1) is synthesized and characterized. It forms aggregates by intermolecular electrostatic interactions and exhibits similar light-harvesting ability as that of conjugated polymers. Efficient fluorescence resonance energy transfer (FRET) occurs from OF-1 to double-stranded DNA tagged with fluorescein (dsDNA-F1). A photoresponsive oligofluorene (OF-3) is also synthesized by protecting OF-1 with 1-(2-nitrophenyl)ethanol. Photolysis of OF-3 can produce OF-1 to result in a fluorescence "turn-on" response, thus the FRET from OF-3 to dsDNA-F1 can be turned on by light irradiation. OF-3 offers the potential for remote DNA sensing.

引用

页码：2175 / 2180

页数：6

共 30 条

[1] Fluorescence superquenching of conjugated polyelectrolytes: applications for biosensing and drug discovery [J].

Achyuthan, KE ;

Bergstedt, TS ;

Chen, L ;

Jones, RM ;

Kumaraswamy, S ;

Kushon, SA ;

Ley, KD ;

Lu, L ;

McBranch, D ;

Mukundan, H ;

Rininsland, F ;

Shi, X ;

Xia, W ;

Whitten, DG .

JOURNAL OF MATERIALS CHEMISTRY, 2005, 15 (27-28) :2648-2656

[2]

[Anonymous], ANGEW CHEM, DOI DOI 10.1002/ANGE.200600214

[3] Highly ordered structures of amphiphilic polythiophenes in aqueous media [J].

Brustolin, F ;

Goldoni, F ;

Meijer, EW ;

Sommerdijk, NAJM .

MACROMOLECULES, 2002, 35 (03) :1054-1059

[4] Poly(aryleneethynylene)s: Syntheses, properties, structures, and applications [J].

Bunz, UHF .

CHEMICAL REVIEWS, 2000, 100 (04) :1605-1644

[5] Cationic Conjugated Polymers for Optical Detection of DNA Methylation, Lesions, and Single Nucleotide Polymorphisms [J].

Duan, Xinrui ;

Liu, Libing ;

Feng, Fude ;

Wang, Shu .

ACCOUNTS OF CHEMICAL RESEARCH, 2010, 43 (02) :260-270

[6] Single-nucleotide polymorphism (SNP) genotyping using cationic conjugated polymers in homogeneous solution [J].

Duan, Xinrui ;

Yue, Wei ;

Liu, Libing ;

Li, Zhengping ;

Li, Yuliang ;

He, Fuchu ;

Zhu, Daoben ;

Zhou, Gangqiao ;

Wang, Shu .

NATURE PROTOCOLS, 2009, 4 (06) :984-991

[7] Fluorescent conjugated polyelectrolyte as an indicator for convenient detection of DNA methylation [J].

Feng, Fude ;

Wang, Hongzhong ;

Han, Lingli ;

Wang, Shu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (34) :11338-11343

[8] Fluorescent conjugated polyelectrolytes for biomacromolecule detection [J].

Feng, Fude ;

He, Fang ;

An, Lingling ;

Wang, Shu ;

Li, Yuhang ;

Zhu, Daoben .

ADVANCED MATERIALS, 2008, 20 (15) :2959-2964

[9] DNA detection using water-soluble conjugated polymers and peptide nucleic acid probes [J].

Gaylord, BS ;

Heeger, AJ ;

Bazan, GC .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (17) :10954-10957

[10] Light-regulated release of DNA and its delivery to nuclei by means of photolabile gold nanoparticles [J].

Han, Gang ;

You, Chang-Cheng ;

Kim, Byoung-Jin ;

Turingan, Rosemary S. ;

Forbes, Neil S. ;

Martin, Craig T. ;

Rotello, Vincent M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (19) :3165-3169

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