Synthesis and photophysical properties of a highly fluorescent ditopic ligand based on 1,6-bis(ethynyl)pyrene as central aromatic core

被引:39
作者
Leroy-Lhez, S
Fages, F
机构
[1] Univ Angers, CNRS, CIMMA, UMR 6200, F-49045 Angers, France
[2] Univ Mediterranee, CNRS, GCOM2, UMR 6114,Case, F-13288 Marseille, France
关键词
pyrene; 2,2'-bipyridine; fluorescence; synthesis; conjugated oligomer;
D O I
10.1002/ejoc.200500059
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple synthetic route for the efficient preparation and purification of two regioisomers of a pyrene derivative containing two ethynyl groups-1,6- and 1,8-bis(ethynyl)pyrene-is described. The former compound was used as a building block for the stepwise synthesis of a highly conjugated, ditopic bis(2,2'-bipyridine) ligand (2) containing the pyrene nucleus at the central core. The fluorescence properties of ligand 2 are reported. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).
引用
收藏
页码:2684 / 2688
页数:5
相关论文
共 38 条
[1]   Quinoline-containing, conjugated poly(aryleneethynylene)s:: Novel metal and H+-responsive materials [J].
Bangcuyo, CG ;
Rampey-Vaughn, ME ;
Quan, LT ;
Angel, SM ;
Smith, MD ;
Bunz, UHF .
MACROMOLECULES, 2002, 35 (05) :1563-1568
[2]   Dynamic chemical devices: Modulation of photophysical properties by reversible, ion-triggered, and proton-fuelled nanomechanical shape-flipping molecular motions [J].
Barboiu, M ;
Prodi, L ;
Montalti, M ;
Zaccheroni, N ;
Kyritsakas, N ;
Lehn, JM .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (12) :2953-2959
[3]   A general purpose reporter for cations: absorption, fluorescence and electrochemical sensing of zinc(II) [J].
Benniston, AC ;
Harriman, A ;
Lawrie, DJ ;
Mayeux, A ;
Rafferty, K ;
Russell, OD .
DALTON TRANSACTIONS, 2003, (24) :4762-4769
[4]   Metal-induced self-assembly of a pyrene-tethered hydroxamate ligand for the generation of multichromophoric supramolecular systems. The pyrene excimer as switch for iron(III)-driven intramolecular fluorescence quenching [J].
Bodenant, B ;
Fages, F ;
Delville, MH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (30) :7511-7519
[5]   Synthesis and ionochromic properties of chelating conjugated polymers [J].
Bouachrine, M ;
Lère-Porte, JP ;
Moreau, JJE ;
Serein-Spirau, F ;
Torreilles, C .
JOURNAL OF MATERIALS CHEMISTRY, 2000, 10 (02) :263-268
[6]  
CHAIKOVSKII VK, 1984, J ORG CHEM USSR, V20, P1350
[7]   Pyrene-bridged bis(phenanthroline) ligands and their dinuelear ruthenium(II) complexes [J].
Chouai, L ;
Wu, FY ;
Jang, YC ;
Thummel, RP .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2003, (15) :2774-2782
[8]   Efficient synthesis of 4,5,9,10-tetrahydropyrene: A useful synthetic intermediate for the synthesis of 2,7-disubstituted pyrenes [J].
Connor, DM ;
Allen, SD ;
Collard, DM ;
Liotta, CL ;
Schiraldi, DA .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) :6888-6890
[9]   New molecular systems for functional dye-based molecular switching of luminescence [J].
Daub, J ;
Beck, M ;
Knorr, A ;
Spreitzer, H .
PURE AND APPLIED CHEMISTRY, 1996, 68 (07) :1399-1404
[10]   1,3,6,8-tetraphenylpyrene derivatives:: Towards fluorescent liquid-crystalline columns? [J].
de Halleux, V ;
Calbert, JP ;
Brocorens, P ;
Cornil, J ;
Declercq, JP ;
Brédas, JL ;
Geerts, Y .
ADVANCED FUNCTIONAL MATERIALS, 2004, 14 (07) :649-659