Synthesis and single-crystal X-ray characterization of 4,4"-functionalized 4′(4-bromophenyl)-2,2′:6′,2"-terpyridines

被引:75
作者
Eryazici, I
Moorefield, CN
Durmus, S
Newkome, GR [1 ]
机构
[1] Univ Akron, Dept Polymer Sci, Akron, OH 44325 USA
[2] Univ Akron, Dept Chem, Akron, OH 44325 USA
[3] Univ Akron, Maurice Morton Inst Polymer Sci, Akron, OH 44325 USA
关键词
D O I
10.1021/jo052036l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
To expand the utility of bis(terpyridine) metal connectivity, the selective symmetrical and unsymmetrical 4,4"-functionalization (-CN, -Me, -CO2Me) of 4'-(4-bromophenyl)-2,2':6',2"-terpyridines was achieved using the Krohnke synthesis The final substituted 2,2':6',2"-terpyridines along with their corresponding intermediates, 4a-c, were recrystallized and characterized by H-1 NMR and C-13 NMR as well as X-ray crystallography; COSY correlations were also conducted to permit definitive proton assignment.
引用
收藏
页码:1009 / 1014
页数:6
相关论文
共 55 条
[1]   Design of novel efficient sensitizing dye for nanocrystalline TiO2 solar cell; tripyridine-thiolato (4,4′,4"-tricarboxy-2,2′:6′,2"-terpyridine)ruthenium(II) [J].
Aiga, F ;
Tada, T .
SOLAR ENERGY MATERIALS AND SOLAR CELLS, 2005, 85 (03) :437-446
[2]   THE COORDINATION CHEMISTRY OF 4'-PHENYL-2,2'-6',2''-TERPYRIDINE - THE SYNTHESIS, CRYSTAL AND MOLECULAR-STRUCTURES OF 4'-PHENYL-2,2'-6',2''-TERPYRIDINE AND BIS(4'-PHENYL-2,2'-6',2''-TERPYRIDINE)NICKEL(II) CHLORIDE DECAHYDRATE [J].
CONSTABLE, EC ;
LEWIS, J ;
LIPTROT, MC ;
RAITHBY, PR .
INORGANICA CHIMICA ACTA, 1990, 178 (01) :47-54
[3]  
CONSTABLE EC, 1992, NEW J CHEM, V16, P855
[4]   Development of supramolecular structure through alkylation of pendant pyridyl functionality [J].
Constable, EC ;
Housecroft, CE ;
Neuburger, M ;
Phillips, D ;
Raithby, PR ;
Schofield, E ;
Sparr, E ;
Tocher, DA ;
Zehnder, M ;
Zimmermann, Y .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2000, (13) :2219-2228
[5]   White-light emission from an assembly comprising luminescent iridium and europium complexes [J].
Coppo, P ;
Duati, M ;
Kozhevnikov, VN ;
Hofstraat, JW ;
De Cola, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (12) :1806-1810
[6]   Reversible colorimetric probes for mercury sensing [J].
Coronado, E ;
Galán-Mascaros, JR ;
Martí-Gastaldo, C ;
Palomares, E ;
Durrant, JR ;
Vilar, R ;
Gratzel, M ;
Nazeeruddin, MK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (35) :12351-12356
[7]   A silver-catalyzed intramolecular amidation of saturated C-H bonds [J].
Cui, Y ;
He, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (32) :4210-4212
[8]   Efficient aziridination of olefins catalyzed by a unique disilver(I) compound [J].
Cui, Y ;
He, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (52) :16202-16203
[9]   First direct C-2-lithiation of 4-DMAP. Convenient access to reactive functional derivatives and ligands [J].
Cuperly, D ;
Gros, P ;
Fort, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :238-241
[10]   Facile synthesis of polypyridine esters: A route to functionalized aldehydes [J].
El-ghayoury, A ;
Ziessel, R .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) :7757-7763