Acceleration of Singlet Fission in an Aza-Derivative of TIPS-Pentacene

被引:91
作者
Herz, Julia [1 ]
Buckup, Tiago [1 ]
Paulus, Fabian [2 ]
Engelhart, Jens [2 ]
Bunz, Uwe H. F. [2 ,3 ]
Motzkus, Marcus [1 ,3 ]
机构
[1] Heidelberg Univ, Phys Chem Inst, D-69120 Heidelberg, Germany
[2] Heidelberg Univ, Organ Chem Inst, D-69120 Heidelberg, Germany
[3] Heidelberg Univ, Ctr Adv Mat, D-69120 Heidelberg, Germany
关键词
THIN-FILM TRANSISTORS; EXCITON-FISSION; TRANSIENT ABSORPTION; TRANSPORT; DYNAMICS; STATE;
D O I
10.1021/jz501102r
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The influence of the carbon to nitrogen substitution on the photoinduced dynamics of TIPS-pentacene was investigated by ultrafast transient absorption measurements on spin-coated thin films in the visible and in the near-infrared spectral region. A global target analysis was performed to provide a detailed picture of the excited-state dynamics. We found that the chemical modification has a high impact on the triplet formation and leads to shorter dynamics; hence it speeds up the singlet fission process. A faster relaxation from the singlet into the triplet manifold implies a higher efficiency because other relaxation channels are avoided. The air-stable aza-derivatives have the potential to exceed the energy conversion efficiency of TIPS-pentacene.
引用
收藏
页码:2425 / 2430
页数:6
相关论文
共 33 条
[1]   Functionalized pentacene: Improved electronic properties from control of solid-state order [J].
Anthony, JE ;
Brooks, JS ;
Eaton, DL ;
Parkin, SR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (38) :9482-9483
[2]   Effects of electronegative substitution on the optical and electronic properties of acenes and diazaacenes [J].
Appleton, Anthony Lucas ;
Brombosz, Scott M. ;
Barlow, Stephen ;
Sears, John S. ;
Bredas, Jean-Luc ;
Marder, Seth R. ;
Bunz, Uwe H. F. .
NATURE COMMUNICATIONS, 2010, 1
[3]   Ultrafast multiphoton transient absorption of β-carotene [J].
Buckup, Tiago ;
Weigel, Alexander ;
Hauer, Juergen ;
Motzkus, Marcus .
CHEMICAL PHYSICS, 2010, 373 (1-2) :38-44
[4]   The Dynamics of Singlet Fission in Crystalline Tetracene and Covalent Analogs [J].
Burdett, Jonathan J. ;
Bardeen, Christopher J. .
ACCOUNTS OF CHEMICAL RESEARCH, 2013, 46 (06) :1312-1320
[5]   Observing the Multiexciton State in Singlet Fission and Ensuing Ultrafast Multielectron Transfer [J].
Chan, Wai-Lun ;
Ligges, Manuel ;
Jailaubekov, Askat ;
Kaake, Loren ;
Miaja-Avila, Luis ;
Zhu, X. -Y. .
SCIENCE, 2011, 334 (6062) :1541-1545
[6]   External Quantum Efficiency Above 100% in a Singlet-Exciton-Fission-Based Organic Photovoltaic Cell [J].
Congreve, Daniel N. ;
Lee, Jiye ;
Thompson, Nicholas J. ;
Hontz, Eric ;
Yost, Shane R. ;
Reusswig, Philip D. ;
Bahlke, Matthias E. ;
Reineke, Sebastian ;
Van Voorhis, Troy ;
Baldo, Marc A. .
SCIENCE, 2013, 340 (6130) :334-337
[7]   Ambipolar transport in organic conjugated material [J].
Cornil, Jerome ;
Bredas, Jean-Luc ;
Zaumseil, Jana ;
Sirringhaus, Henning .
ADVANCED MATERIALS, 2007, 19 (14) :1791-1799
[8]  
Dimitrakopoulos CD, 2002, ADV MATER, V14, P99, DOI 10.1002/1521-4095(20020116)14:2<99::AID-ADMA99>3.0.CO
[9]  
2-9
[10]   Pd-Catalyzed Coupling of Non-Activated Dibromoarenes to 2,3-Diaminoarenes: Formation of N, N′-Dihydropyrazines [J].
Engelhart, Jens U. ;
Lindner, Benjamin D. ;
Tverskoy, Olena ;
Rominger, Frank ;
Bunz, Uwe H. F. .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (45) :15089-15092