Novel fluorescent pH sensors based on intramolecular hydrogen bonding ability of naphthalimide

被引：102

作者：

Cui, DW ^{[1
]}

Qian, XH ^{[1
]}

Liu, FY ^{[1
]}

Zhang, R ^{[1
]}

机构：

[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116012, Liaoning Provin, Peoples R China

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 16期

关键词：

D O I：

10.1021/ol049005h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4-Piperidine-naphthalimide derivatives containing potential acceptors for hydrogen bonding were synthesized, and their fluorescence properties were examined. Some of the compounds with a 2-imino-oxalidin (thiazolidin) side chain at the imide moiety exhibit a strong fluorescence quench and some red shift in weakly acidic conditions, caused by the formation of an intramolecular hydrogen bond. Their pK(a), values were estimated to be about 6.4-7.5. The results showed that these compounds could serve as novel fluorescent pH sensors for further application.

引用

页码：2757 / 2760

页数：4

共 19 条

[1] THE UV-VISIBLE ABSORPTION AND FLUORESCENCE OF SOME SUBSTITUTED 1,8-NAPHTHALIMIDES AND NAPHTHALIC ANHYDRIDES [J].

ALEXIOU, MS ;

TYCHOPOULOS, V ;

GHORBANIAN, S ;

TYMAN, JHP ;

BROWN, RG ;

BRITTAIN, PI .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1990, (05) :837-842

[2]

BENRARD V, 2001, MOL FLUORESCENCE PRI, pCH10

[3]

Brana M. F., 2001, Current Medicinal Chemistry - Anti-Cancer Agents, V1, P237, DOI 10.2174/1568011013354624

[4]

de Silva AP, 1999, CHEM COMMUN, P163

[5] NEW FLUORESCENT MODEL COMPOUNDS FOR THE STUDY OF PHOTOINDUCED ELECTRON-TRANSFER - THE INFLUENCE OF A MOLECULAR ELECTRIC-FIELD IN THE EXCITED-STATE [J].

DE SILVA, AP ;

GUNARATNE, HQN ;

HABIBJIWAN, JL ;

MCCOY, CP ;

RICE, TE ;

SOUMILLION, JP .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (16) :1728-1731

[6] Signaling recognition events with fluorescent sensors and switches [J].

de Silva, AP ;

Gunaratne, HQN ;

Gunnlaugsson, T ;

Huxley, AJM ;

McCoy, CP ;

Rademacher, JT ;

Rice, TE .

CHEMICAL REVIEWS, 1997, 97 (05) :1515-1566

[7]

DECOSTA MDP, 1987, CAN J CHEM, V65, P1416, DOI 10.1139/v87-239

[8] Radiationless deactivation of excited molecules of 4-aminonaphthalimides [J].

Dmitruk, SL ;

Druzhinin, SI ;

Minakova, RA ;

Bedrik, AI ;

Uzhinov, BM .

RUSSIAN CHEMICAL BULLETIN, 1997, 46 (12) :2027-2031

[9]

GUILFORD J, 2001, J PHOTOCH PHOTOBIO B, V65, P5

[10]

HEIKO I, 2000, ORG LETT, V2, P2865

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