Naphtho[4,3,2,1-lmn][2,9]phenanthrolines: Synthesis, characterization, optical properties and light-induced electron transfer in composites with the semiconducting polymer MEH-PPV

被引：9

作者：

Baranov, Denis S. ^{[1
,2
]}

Popov, Alexandr G. ^{[1
,2
]}

Uvarov, Mikhail N. ^{[1
]}

Kazantsev, Maxim S. ^{[2
,3
]}

Mostovich, Evgeny A. ^{[2
,3
]}

Glebov, Evgeni M. ^{[1
,2
]}

Kulik, Leonid V. ^{[1
,2
]}

机构：

[1] Russian Acad Sci, Siberian Branch, VV Voevodsky Inst Chem Kinet & Combust, Novosibirsk 630090, Russia

[2] Novosibirsk State Univ, Novosibirsk 630090, Russia

[3] Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia

来源：

SYNTHETIC METALS | 2015年 / 201卷

关键词：

Diazapyrenes; Synthesis; Spectroscopy; Light-induced electron transfer; BASIS-SETS; POLARONS; DESIGN; ESR;

D O I：

10.1016/j.synthmet.2015.01.012

中图分类号：

T [工业技术];

学科分类号：

08 ;

摘要：

Novel naphtho[4,3,2,1-lmn][2,9]phenanthrolines were synthesized via reaction between 1,5-diethynyl-9,10-anthraquinones and urea in DMF. Their HOMO and LUMO levels determined from optical spectroscopy and cyclic voltammetry are in good agreement with those determined from quantum chemical calculation. Light-induced electron transfer from the semiconducting polymer MEH-PPV to the synthesized molecules was detected by EPR-spectroscopy, showing their possible applicability as electron acceptors in bulk heterojunction organic solar cells. The synthesized naphtho[4,3,2,1-lmn][2,9]phenanthrolines can be used as building blocks for larger molecules with an extended pi-conjugated system, which can be used as acceptors in organic photovoltaics. (C) 2015 Elsevier B.V. All rights reserved.

引用

页码：43 / 48

页数：6

共 25 条

[1] Gabedit-A Graphical User Interface for Computational Chemistry Softwares [J].

Allouche, Abdul-Rahman .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 2011, 32 (01) :174-182

[2] Synthesis of benzo[de]isoquino[1,8-gh]quinolines and light-induced electron transfer in their composites with conductive polymer poly(3-hexylthiophene) [J].

Baranov, Denis S. ;

Popov, Aleksandr G. ;

Uvarov, Mikhail N. ;

Kulik, Leonid V. .

MENDELEEV COMMUNICATIONS, 2014, 24 (06) :383-385

[3]

Brabec C.J., 2010, Organic Photovoltaics: Concepts and Realization

[4] Large N-Heteroacenes: New Tricks for Very Old Dogs? [J].

Bunz, Uwe H. F. ;

Engelhart, Jens U. ;

Lindner, Benjamin D. ;

Schaffroth, Manuel .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (14) :3810-3821

[5] Rational design on n-type organic materials for high performance organic photovoltaics [J].

Chochos, Christos L. ;

Tagmatarchis, Nikos ;

Gregoriou, Vasilis G. .

RSC ADVANCES, 2013, 3 (20) :7160-7181

[6] REFERENCE MATERIALS FOR FLUORESCENCE MEASUREMENT [J].

EATON, DF .

PURE AND APPLIED CHEMISTRY, 1988, 60 (07) :1107-1114

[7] Effect of the Damping Function in Dispersion Corrected Density Functional Theory [J].

Grimme, Stefan ;

Ehrlich, Stephan ;

Goerigk, Lars .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 2011, 32 (07) :1456-1465

[8] A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu [J].

Grimme, Stefan ;

Antony, Jens ;

Ehrlich, Stephan ;

Krieg, Helge .

JOURNAL OF CHEMICAL PHYSICS, 2010, 132 (15)

[9]

Higgins R.W., 1939, J AM CHEM SOC, V61, P2662

[10] Perylene diimides based materials for organic solar cells [J].

Kozma, Erika ;

Catellani, Marinella .

DYES AND PIGMENTS, 2013, 98 (01) :160-179

← 1 2 3 →