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Prediction and Theoretical Characterization of p-Type Organic Semiconductor Crystals for Field-Effect Transistor Applications

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Prediction and Calculation of Crystal Structures

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 345))

Abstract

The theoretical prediction and characterization of the solid-state structure of organic semiconductors has tremendous potential for the discovery of new high performance materials. To date, the theoretical analysis mostly relied on the availability of crystal structures obtained through X-ray diffraction. However, the theoretical prediction of the crystal structures of organic semiconductor molecules remains a challenge. This review highlights some of the recent advances in the determination of structure–property relationships of the known organic semiconductor single-crystals and summarizes a few available studies on the prediction of the crystal structures of p-type organic semiconductors for transistor applications.

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Abbreviations

BTBT:

[1]Benzothieno[3,2-b][1]benzothiophene

BTBT-C8 :

2,7-Dioctyl[1]benzothieno[3,2-b][1]benzothiophene

DATT:

Dianthra[2,3-b:2′,3′-f]thieno[3,2-b]thiophene

DMA:

Distributed multipole analysis

DNTT:

Dinaphtha[2,3-b:2′,3′-f]thieno[3,2-b]thiophene

DPP:

Diketo-pyrrolo-pyrrole

DPP(TBFu)2 :

3,6-Bis(5-(benzofuran-2-yl)thiophen-2-yl)-2,5-bis(2- ethylhexyl)pyrrolo[3,4-c]pyrrole-1,4-dione

DTT-Ph-C(8,12):

2,6-Bis(4-{octyl,dodecyl}phenyl)-dithieno[3,2-b′:2′,3′-d]thiophene

GA:

Genetic algorithms

ISC:

Inorganic semiconductor

OSC:

Organic semiconductor

PDIF-CN2 :

N,N′-1H,1H-Perfluorobutyldicyanoperylene-carboxydi-imide

Rubrene:

5,6,11,12-Tetraphenyltetracene

TbTH:

Tetraceno[2,3-b]thiophene

TcTH:

Tetraceno[2,3-c]thiophene

Tips-pentacene:

6,13-Bis(triisopropylsilylethynyl)pentacene

TMTSF:

Tetramethyltetraselenafulvalene

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Acknowledgements

We thank Semion Saikin and Stéphanie Valleau for stimulating discussions and reading the manuscript. We acknowledge computing facilities at the High Performance Technical Center at the Faculty of Art and Science of Harvard University, XSEDE/Teragrid resources supported by National Science Foundation award number OCI-1053575, and software support from ChemAxon Ltd.

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  1. Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA, 02138, USA

    Şule Atahan-Evrenk & Alán Aspuru-Guzik

  2. TOBB-ETU Medical School, Sogutozu Cad. No: 43, Sogutozu, Ankara, 06560, Turkey

    Şule Atahan-Evrenk

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  1. Şule Atahan-Evrenk
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Correspondence to Şule Atahan-Evrenk .

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  1. Dept. of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts, USA

    Sule Atahan-Evrenk

  2. Dept. of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts, USA

    Alan Aspuru-Guzik

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Atahan-Evrenk, Ş., Aspuru-Guzik, A. (2014). Prediction and Theoretical Characterization of p-Type Organic Semiconductor Crystals for Field-Effect Transistor Applications. In: Atahan-Evrenk, S., Aspuru-Guzik, A. (eds) Prediction and Calculation of Crystal Structures. Topics in Current Chemistry, vol 345. Springer, Cham. https://doi.org/10.1007/128_2013_526

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