Synthesis and Structures of Multifunctionalized Helicenes and Dehydrohelicenes: An Efficient Route to Construct Cyan Fluorescent Molecules

被引：45

作者：

Chen, Jun-Dao ^{[1
,2
]}

Lu, Hai-Yan ^{[2
]}

Chen, Chuan-Feng ^{[1
]}

机构：

[1] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China

[2] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 39期

基金：

中国国家自然科学基金;

关键词：

fluorescence; functionalization; helicenes; helical structures; synthetic methods; ENANTIOSELECTIVE SYNTHESIS; DERIVATIVES; RESOLUTION; RINGS;

D O I：

10.1002/chem.201001655

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Spiral up! A series of multifunctionalized benzo[5]helicene derivatives and a benzo[7]helicene were conveniently synthesized. Moreover, the oxidative cyclodehydrogenation of the benzo[5]helicenes by DDQ in trifluoroacetic acid or trifluoromethanesulfonic acid quantitatively provided the corresponding dehydro[5]helicene derivatives, which showed the cyan fluorescent properties (shown here). © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：11843 / 11846

页数：4

共 54 条

[1]

[Anonymous], 2001, ANGEW CHEM

[2] Towards configurationally stable [4]helicenes:: Enantioselective synthesis of 12-substituted 7,8-dihydro[4]helicene quinones [J].

Carreno, M. Carmen ;

Enriquez, Alvaro ;

Garcia-Cerrada, Susana ;

Sanz-Cuesta, M. Jesus ;

Urbano, Antonio ;

Maseras, Feliu ;

Nonell-Canals, Alfons .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (02) :603-620

[3] Efficient asymmetric synthesis of [7]helicene bisquinones [J].

Carreño, MC ;

González-López, M ;

Urbano, A .

CHEMICAL COMMUNICATIONS, 2005, (05) :611-613

[4] From central to helical chirality:: Synthesis of P and M enantiomers of [5]helicenequinones and bisquinones from (SS)-2-(p-tolylsulfinyl)-1,4-benzoquinone [J].

Carreño, MC ;

García-Cerrada, S ;

Urbano, A .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (17) :4118-4131

[5] Enantiopure dihydro-[5]-helicenequinones via Diels-Alder reactions of vinyl dihydrophenanthrenes and (SS)-2-(p-tolylsulfinyl)-1,4-benzoquinone [J].

Carreño, MC ;

García-Cerrada, S ;

Urbano, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (32) :7929-7930

[6]

Collins S.K., 2006, Angew. Chem, V118, P2989

[7] Preparation of helicenes through olefin metathesis [J].

Collins, Shawn K. ;

Grandbois, Alain ;

Vachon, Martin P. ;

Cote, Julie .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (18) :2923-2926

[8] DEHYDROGENATION OF HETEROHELICENES BY A SCHOLL TYPE REACTION - DEHYDROHELICENES [J].

DOPPER, JH ;

OUDMAN, D ;

WYNBERG, H .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (23) :3398-3401

[9] Application of the Russig-Laatsch reaction to synthesize a bis[5]helicene chiral pocket for asymmetric catalysis [J].

Dreher, SD ;

Katz, TJ ;

Lam, KC ;

Rheingold, AL .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (03) :815-822

[10] Easy synthesis of functionalized hetero[7]helicenes [J].

Dreher, SD ;

Weix, DJ ;

Katz, TJ .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3671-3678

← 1 2 3 4 5 6 →