Synthesis and characterization of some Aza[5]helicenes

被引：83

作者：

Bazzini, C

Brovelli, S

Caronna, T

Gambarotti, C

Giannone, M

Macchi, P

Meinardi, F

Mele, A

Panzeri, W

Recupero, F

Sironi, A

Tubino, R

机构：

[1] Univ Bergamo, Dipartimento Ingn Ind, I-24044 Dalmine, Italy

[2] Univ Milano Bicocca, INFM, I-20125 Milan, Italy

[3] Univ Milano Bicocca, Dipartimento Sci Mat, I-20125 Milan, Italy

[4] Politecn Milan, Dipartimento Chim Mat & Ingn Chim G Natta, I-20131 Milan, Italy

[5] Univ Milan, Dipartimento Chim Strutturale & Stereochim Inorga, I-20133 Milan, Italy

[6] CNR, Ist Chim Riconosci Mol, I-20131 Milan, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 07期

关键词：

helical structures; fluorescence spectroscopy; photochemistry;

D O I：

10.1002/ejoc.200400648

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A systematic study on the synthesis and properties of aza[5]helicenes bearing one or two nitrogen atoms in selected ring positions is reported for the first time. This photochemical approach can be conveniently applied to the preparation of either mono- or diaza[5]helicenes. The aza[5]helicenes were characterized by NMR spectroscopy, X-ray crystallography, emission spectroscopy, and luminescence lifetime. The extremely long triplet lifetime observed (in the range of seconds) makes these molecules promising candidates for practical applications in photo- and optoelectronics.

引用

页码：1247 / 1257

页数：11

共 87 条

[1] CAMBRIDGE CRYSTALLOGRAPHIC DATA CENTER - COMPUTER-BASED SEARCH, RETRIEVAL, ANALYSIS AND DISPLAY OF INFORMATION [J].

ALLEN, FH ;

BELLARD, S ;

BRICE, MD ;

CARTWRIGHT, BA ;

DOUBLEDAY, A ;

HIGGS, H ;

HUMMELINK, T ;

HUMMELINKPETERS, BG ;

KENNARD, O ;

MOTHERWELL, WDS ;

RODGERS, JR ;

WATSON, DG .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1979, 35 (OCT) :2331-2339

[2] SIR97:: a new tool for crystal structure determination and refinement [J].

Altomare, A ;

Burla, MC ;

Camalli, M ;

Cascarano, GL ;

Giacovazzo, C ;

Guagliardi, A ;

Moliterni, AGG ;

Polidori, G ;

Spagna, R .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1999, 32 :115-119

[3] CONFORMATIONAL EQUILIBRIA IN TRANS-DIARYLETHYLENES - SPECTRAL AND PHOTOPHYSICAL PROPERTIES OF ROTAMERS OF 1-(2-NAPHTHYL)-2-(6'-QUINOLYL)ETHYLENE, DERIVED FROM KINETIC AND STATISTICAL FLUORESCENCE ANALYSIS [J].

BARTOCCI, G ;

SPALLETTI, A ;

MASETTI, F ;

CRUCIANI, G .

JOURNAL OF MOLECULAR STRUCTURE, 1993, 298 :165-175

[4]

BARTON JW, 1978, TETRAHEDRON LETT, P1005

[5] COMPOUNDS WITH A HELIX STRUCTURE .1. SYNTHESIS AND ABSOLUTE-CONFIGURATION OF (+)-PENTAHELICENE [J].

BESTMANN, HJ ;

BOTH, W .

CHEMISCHE BERICHTE-RECUEIL, 1974, 107 (09) :2923-2925

[6]

BIRKS JB, 1970, PHOTOPHYSICS ORGANIC

[7]

BORTOLUS P, 1966, TETRAHEDRON LETT, P239

[8] 4-Quinolylmethyl and 1-naphthylmethyl as benzyl-type protecting groups of carboxylic acids removable by homogeneous palladium-catalyzed hydrogenolysis [J].

Boutros, A ;

Legros, JY ;

Fiaud, JC .

TETRAHEDRON, 2000, 56 (15) :2239-2246

[9] OMEGA-HALOGENOMETHYL-PYRIDINES, OMEGA-HALOGENOMETHYL-EQUINOLINES, AND OMEGA-HALOGENOMETHYL-ISOQUINOLINES [J].

BROWN, BR ;

HAMMICK, DL ;

THEWLIS, BH .

JOURNAL OF THE CHEMICAL SOCIETY, 1951, (MAY) :1145-1149

[10]

Caronna T, 2002, HELV CHIM ACTA, V85, P1

← 1 2 3 4 5 6 7 8 9 →