Cyclo[2]benzimidazole: luminescence turn-on sensing of anions

被引:33
作者
Abraham, Yael [1 ]
Salman, Husein [1 ]
Suwinska, Kinga [2 ]
Eichen, Yoav [1 ]
机构
[1] Technion Israel Inst Technol, Schulich Fac Chem, IL-32000 Haifa, Israel
[2] Polish Acad Sci, PL-01224 Warsaw, Poland
关键词
INTRAMOLECULAR PROTON-TRANSFER; FLUORESCENT CHEMOSENSOR; ALKYLATING-AGENTS; RECOGNITION; SENSORS; IDENTIFICATION; RECEPTORS; MOLECULES; EMISSION; BINDING;
D O I
10.1039/c1cc10995b
中图分类号
O6 [化学];
学科分类号
070301 [无机化学];
摘要
Cyclo[2]benzimidazole is a new host for anions that turns on its luminescence up to 150 fold upon binding. Photoexcited cyclo[2]benzimidazole undergoes an efficient non-radiative deactivation through an excited-state intramolecular proton-transfer (ESIPT) mechanism. Upon binding an anion, the ESIPT pathway is blocked, resulting in an increase in the luminescence efficiency.
引用
收藏
页码:6087 / 6089
页数:3
相关论文
共 43 条
[1]
[Anonymous], 1993, Fluorescent chemosensors for ion and molecule recognition, DOI DOI 10.1080/10739149408001201
[2]
EXCITED-STATE PROTON-TRANSFER REACTIONS .1. FUNDAMENTALS AND INTERMOLECULAR REACTIONS [J].
ARNAUT, LG ;
FORMOSINHO, SJ .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1993, 75 (01) :1-20
[3]
Towards an omnipotent "Artificial Nose": detection and identification of alkylating agents using an optical sensor array [J].
Borzin, Elena ;
Shemesh, Ariel ;
Hertzog-Ronen, Carmit ;
Gerchikov, Yulia ;
Tessler, Nir ;
Eichen, Yoav .
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2010, 23 (11) :1108-1113
[4]
ION-RESPONSIVE FLUORESCENT COMPOUNDS .4. EFFECT OF CATION BINDING ON THE PHOTOPHYSICAL PROPERTIES OF A COUMARIN LINKED TO MONOAZA-CROWN AND DIAZA-CROWN ETHERS [J].
BOURSON, J ;
POUGET, J ;
VALEUR, B .
JOURNAL OF PHYSICAL CHEMISTRY, 1993, 97 (17) :4552-4557
[5]
Lanthanide Luminescence for Biomedical Analyses and Imaging [J].
Buenzli, Jean-Claude G. .
CHEMICAL REVIEWS, 2010, 110 (05) :2729-2755
[6]
Luminescent sensors and switches in the early 21st century [J].
Callan, JF ;
de Silva, AP ;
Magri, DC .
TETRAHEDRON, 2005, 61 (36) :8551-8588
[7]
EXCITED-STATE INTRAMOLECULAR PROTON-TRANSFER IN 2-(2'-HYDROXYPHENYL)BENZIMIDAZOLE AND 2-(2'-HYDROXYPHENYL)-BENZOXAZOLE - EFFECT OF ROTAMERISM AND HYDROGEN-BONDING [J].
DAS, K ;
SARKAR, N ;
GHOSH, AK ;
MAJUMDAR, D ;
NATH, DN ;
BHATTACHARYYA, K .
JOURNAL OF PHYSICAL CHEMISTRY, 1994, 98 (37) :9126-9132
[8]
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
[9]
Fluorescent sensing of anions using a bis-quinoxaline amidothiourea based supramolecular cleft; an example of an anion-induced deprotonation event [J].
Duke, Rebecca M. ;
Gunnlaugsson, Thorfinnur .
TETRAHEDRON LETTERS, 2010, 51 (41) :5402-5405
[10]
Luminescence anion sensing via modulation of MLCT emission from a naphthalimide-Ru(II)-polypyridyl complex [J].
Elmes, Robert B. P. ;
Gunnlaugsson, Thorfinnur .
TETRAHEDRON LETTERS, 2010, 51 (31) :4082-4087