Triphenylamine-based receptor for selective recognition of dicarboxylates

被引:40
作者
Ghosh, Kumaresh [1 ]
Saha, Indrajit [1 ]
Masanta, Goutam [1 ]
Wang, Evan B. [2 ]
Parish, Carol A. [2 ]
机构
[1] Univ Kalyani, Dept Chem, Kalyani 741235, Nadia, India
[2] Univ Richmond, Dept Chem, Richmond, VA 23173 USA
基金
美国国家科学基金会;
关键词
Triphenylamine; Dicarboxylate ion recognition; Suberate; Fluorescence quenching; Conformational analysis; FLUORESCENT SENSOR; CARBOXYLATE COMPLEXATION; ANION-BINDING; ALPHA; OMEGA-DICARBOXYLATE; FLUORORECEPTOR; LUMINESCENT; INDICATOR; THIOUREA; WATER; MODE;
D O I
10.1016/j.tetlet.2009.11.021
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new triphenylamine-based receptor 1 has been designed and synthesized for the recognition of aliphatic dicarboxylates of various chain lengths. This receptor has been designed to utilize an amide-urea conjugate for binding dicarboxylates. The receptor 1 is found to bind the dicarboxylates with moderate binding strength under a semi rigid, propeller shaped, fluorescent triphenylamine spacer. The binding behavior was studied in CH3CN using H-1 NMR, fluorescence and UV-vis spectroscopic methods. The conformational behavior of 1 and its complexation modes have been investigated using classical and quantum mechanical theoretical methods. The receptor is found to be selective for long chain suberate. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:343 / 347
页数:5
相关论文
共 35 条
[1]  
Bianchi E., 1997, SUPRAMOLECULAR CHEM
[2]   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
[3]   ortho-Phenylenediamine bis-urea-carboxylate:: a new reliable supramolecular synthon [J].
Brooks, SJ ;
Gale, PA ;
Light, ME .
CRYSTENGCOMM, 2005, 7 :586-591
[4]   Carboxylate complexation by a family of easy-to-make ortho-phenylenediamine based bis-ureas:: studies in solution and the solid state [J].
Brooks, SJ ;
Edwards, PR ;
Gale, PA ;
Light, ME .
NEW JOURNAL OF CHEMISTRY, 2006, 30 (01) :65-70
[5]   Carboxylate complexation by 1,1′-(1,2-phenylene)bis(3-phenylurea) in solution and the solid state [J].
Brooks, SJ ;
Gale, PA ;
Light, ME .
CHEMICAL COMMUNICATIONS, 2005, (37) :4696-4698
[6]   Anion binding vs. sulfonamide deprotonation in functionalised ureas [J].
Caltagirone, Claudia ;
Bates, Gareth W. ;
Gale, Philip A. ;
Light, Mark E. .
CHEMICAL COMMUNICATIONS, 2008, (01) :61-63
[7]   Solution and solid-state studies of 3,4-dichloro-2,5-diamidopyrroles: formation of an unusual anionic narcissistic dimer [J].
Camiolo, S ;
Gale, PA ;
Hursthouse, MB ;
Light, ME ;
Shi, AJ .
CHEMICAL COMMUNICATIONS, 2002, (07) :758-759
[8]   Nitrophenyl derivatives of pyrrole 2,5-diamides: structural behaviour, anion binding and colour change signalled deprotonation [J].
Camiolo, S ;
Gale, PA ;
Hursthouse, MB ;
Light, ME .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (04) :741-744
[9]   Selective fluorescent PET sensing of fluoride (F-)using naphthalimide-thiourea and -urea conjugates [J].
Duke, Rebecca M. ;
Gunnlaugsson, Thorfinnur .
TETRAHEDRON LETTERS, 2007, 48 (45) :8043-8047
[10]   Pyrrolylamidourea based anion receptors [J].
Evans, Louise S. ;
Gale, Philip A. ;
Light, Mark E. ;
Quesada, Roberto .
NEW JOURNAL OF CHEMISTRY, 2006, 30 (07) :1019-1025