Facile synthesis and self-assembly of diazafluorenone-based p-n (donor-acceptor) organic semiconductors

被引：13

作者：

Li, Wei-Jie ^{[1
,2
]}

Wu, Hai-Mei ^{[1
,2
]}

Li, Yi-Bao ^{[3
]}

Hu, Chao-Peng ^{[1
,2
]}

Yi, Ming-Dong ^{[1
,2
]}

Xie, Ling-Hai ^{[1
,2
]}

Chen, Lin ^{[1
,2
]}

Zhao, Jian-Feng ^{[1
,2
]}

Zhao, Xiang-Hua ^{[1
,2
]}

Shi, Nai-En ^{[1
,2
]}

Qian, Yan ^{[1
,2
]}

Wang, Chen ^{[4
]}

Wei, Wei ^{[1
,2
]}

Huang, Wei ^{[1
,2
]}

机构：

[1] Nanjing Univ Posts & Telecommun, Jiangsu Singapore Joint Res Ctr Organ Bio Elect &, Nanjing 210046, Jiangsu, Peoples R China

[2] Nanjing Univ Posts & Telecommun, IAM, Nanjing 210046, Jiangsu, Peoples R China

[3] Gannan Normal Univ, Key Lab Organopharmaceut Chem, Ganzhou 341000, Peoples R China

[4] Natl Ctr Nanosci & Technol, Beijing 100190, Peoples R China

来源：

TETRAHEDRON | 2012年 / 68卷 / 39期

基金：

中国国家自然科学基金;

关键词：

2,7-Dibromo-4,5-diazafluoren-9-one; Oxidation and rearrangement mechanism; Self-assembly; p-n (donor-acceptor); Organic semiconductors; LOW-BAND-GAP; MOLECULES; THIOPHENE; POLYMER; OLIGOTHIOPHENES; CHROMOPHORES; PROPERTY; STRENGTH; DIBLOCK;

D O I：

10.1016/j.tet.2012.07.066

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and effective method to prepare 2,7-dibromo-4,5-diazafluoren-9-one (3) has been described involving tandem oxidation and rearrangement reactions. Diazafluorenone-based donor-acceptor (p-n) molecules via stille coupling reactions exhibit solvent-dependent fluorescence and excellent self-assembly behaviors at the solid liquid interface according to the characterization of scanning tunneling microscopy (STM). (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：8216 / 8221

页数：6

共 35 条

[1] Are single molecular wires conducting? [J].

Bumm, LA ;

Arnold, JJ ;

Cygan, MT ;

Dunbar, TD ;

Burgin, TP ;

Jones, L ;

Allara, DL ;

Tour, JM ;

Weiss, PS .

SCIENCE, 1996, 271 (5256) :1705-1707

[2] Achieving high-efficiency non-doped blue organic light-emitting diodes: charge-balance control of bipolar blue fluorescent materials with reduced hole-mobility [J].

Chi, Chih-Chin ;

Chiang, Chih-Long ;

Liu, Shun-Wei ;

Yueh, Han ;

Chen, Chin-Ti ;

Chen, Chao-Tsen .

JOURNAL OF MATERIALS CHEMISTRY, 2009, 19 (31) :5561-5571

[3] s-Tetrazines as Building Blocks for New Functional Molecules and Molecular Materials [J].

Clavier, Gilles ;

Audebert, Pierre .

CHEMICAL REVIEWS, 2010, 110 (06) :3299-3314

[4] Selective and efficient synthesis of di-, tri- and tetrasubstituted 1,10-phenanthrolines [J].

Dietrich-Buchecker, C ;

Jiménez, MC ;

Sauvage, JP .

TETRAHEDRON LETTERS, 1999, 40 (17) :3395-3396

[5] Supramolecular structures of coronene and alkane acids at the Au(111)-solution interface: A scanning tunneling microscopy study [J].

Gyarfas, BJ ;

Wiggins, B ;

Zosel, M ;

Hipps, KW .

LANGMUIR, 2005, 21 (03) :919-923

[6] Highly mobile electrons and holes on isolated chains of the semiconducting polymer poly(phenylenevinylene) [J].

Hoofman, RJOM ;

de Haas, MP ;

Siebbeles, LDA ;

Warman, JM .

NATURE, 1998, 392 (6671) :54-56

[7] Linear Heterocyclic Aromatic Fluorescence Compounds Having Various Donor-Acceptor Spacers Prepared by the Combination of Carbon-Carbon Bond and Carbon-Nitrogen Bond Cross-Coupling Reactions [J].

Hu, Bin ;

Fu, Shu-Jun ;

Xu, Feng ;

Tao, Tao ;

Zhu, Hao-Yu ;

Cao, Kou-Sen ;

Huang, Wei ;

You, Xiao-Zeng .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (11) :4444-4456

[8]

Huang W, 1998, ADV MATER, V10, P593, DOI 10.1002/(SICI)1521-4095(199805)10:8<593::AID-ADMA593>3.0.CO

[9]

2-9

[10] Structural effects on electrical conduction of conjugated molecules studied by scanning tunneling microscopy [J].

Ishida, T ;

Mizutani, W ;

Choi, N ;

Akiba, U ;

Fujihira, M ;

Tokumoto, H .

JOURNAL OF PHYSICAL CHEMISTRY B, 2000, 104 (49) :11680-11688

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