Geometry and Electronic Coupling in Perylenediimide Stacks: Mapping Structure-Charge Transport Relationships

被引：118

作者：

Vura-Weis, Josh

Ratner, Mark A. ^{[1
]}

Wasielewski, Michael R.

机构：

[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 06期

关键词：

NONCOVALENT INTERACTIONS; CRYSTALLOCHROMY; FUNCTIONALS; PERFORMANCE; TRANSISTORS; NAPHTHALENE; OLIGOMERS; DIIMIDES; KINETICS; CRYSTAL;

D O I：

10.1021/ja907761e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The binding energy and electronic coupling of perylenediimide (PDI) pi-stacked dimers were calculated using M06-2X/6-31++G** as a function of stacking geometry. Due to shallow minima in the potential energy surface, electronic coupling can vary by over an order of magnitude among, energetically accessible geometries. The coupling was then determined for 20 PDI derivatives with various substitutions at the imide region, and several were identified as the most promising candidates for organic thin film transistors (OTFTs). This strategy of side-by-side comparison of binding energy and electronic coupling may prove useful for other pi-stacked OTFTs such as pentacene and poly(thiophene) derivatives.

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页码：1738 / +

页数：4

相关论文

共 25 条

[1] CALCULATION OF SMALL MOLECULAR INTERACTIONS BY DIFFERENCES OF SEPARATE TOTAL ENERGIES - SOME PROCEDURES WITH REDUCED ERRORS [J].

BOYS, SF ;

BERNARDI, F .

MOLECULAR PHYSICS, 1970, 19 (04) :553-&

[2] Charge-transfer and energy-transfer processes in π-conjugated oligomers and polymers:: A molecular picture [J].

Brédas, JL ;

Beljonne, D ;

Coropceanu, V ;

Cornil, J .

CHEMICAL REVIEWS, 2004, 104 (11) :4971-5003

[3] Perylenediimide nanowires and their use in fabricating field-effect transistors and complementary inverters [J].

Briseno, Alejandro L. ;

Mannsfeld, Stefan C. B. ;

Reese, Colin ;

Hancock, Jessica M. ;

Xiong, Yujie ;

Jenekhe, Samson A. ;

Bao, Zhenan ;

Xia, Younan .

NANO LETTERS, 2007, 7 (09) :2847-2853

[4] Three-dimensional band structure and bandlike mobility in oligoacene single crystals:: A theoretical investigation [J].

Cheng, YC ;

Silbey, RJ ;

da Silva, DA ;

Calbert, JP ;

Cornil, J ;

Brédas, JL .

JOURNAL OF CHEMICAL PHYSICS, 2003, 118 (08) :3764-3774

[5] Organic thin film transistors based on N-alkyl perylene diimides:: Charge transport kinetics as a function of gate voltage and temperature [J].

Chesterfield, RJ ;

McKeen, JC ;

Newman, CR ;

Ewbank, PC ;

da Silva, DA ;

Brédas, JL ;

Miller, LL ;

Mann, KR ;

Frisbie, CD .

JOURNAL OF PHYSICAL CHEMISTRY B, 2004, 108 (50) :19281-19292

[6] Interaction of Charge Carriers with Lattice Vibrations in Organic Molecular Semiconductors: Naphthalene as a Case Study [J].

Coropceanu, Veaceslav ;

Sanchez-Carrera, Roel S. ;

Paramonov, Pavel ;

Day, Graeme M. ;

Bredas, Jean-Luc .

JOURNAL OF PHYSICAL CHEMISTRY C, 2009, 113 (11) :4679-4686

[7] Transport properties in the rubrene crystal:: Electronic coupling and vibrational reorganization energy [J].

da Silva, DA ;

Kim, EG ;

Brédas, JL .

ADVANCED MATERIALS, 2005, 17 (08) :1072-+

[8]

Feng XL, 2009, NAT MATER, V8, P421, DOI [10.1038/NMAT2427, 10.1038/nmat2427]

[9] Exciton trapping in π-conjugated materials:: A quantum-chemistry-based protocol applied to perylene bisimide dye aggregates [J].

Fink, Reinhold F. ;

Seibt, Joachim ;

Engel, Volker ;

Renz, Manuel ;

Kaupp, Martin ;

Lochbrunner, Stefan ;

Zhao, Hong-Mei ;

Pfister, Johannes ;

Wuerthner, Frank ;

Engels, Bernd .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (39) :12858-+

[10] N,N′-di-4-pyridylperylene-3,4:9,10-bis-(dicarboximide) [J].

Hino, K ;

Sato, K ;

Takahashi, H ;

Suzuki, S ;

Mizuguchi, J .

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 :O440-O441