Solution Processable Pseudo n-Thienoacenes via Intramolecular S···S Lock for High Performance Organic Field Effect Transistors

Sureshraju Vegiraju; Xian Lun Luo; Long Huan Li; Shakil N. Afraj; Chi Lee; Ding Zheng; Hsin Chun Hsieh; Chia Chi Lin; Shao Huan Hong; Hsin Chia Tsai; Gene Hsiang Lee; Shih Huang Tung; Cheng Liang Liu; Ming Chou Chen; Antonio Facchetti

doi:10.1021/acs.chemmater.9b03967

Solution Processable Pseudo n-Thienoacenes via Intramolecular S···S Lock for High Performance Organic Field Effect Transistors

Sureshraju Vegiraju, Xian Lun Luo, Long Huan Li, Shakil N. Afraj, Chi Lee, Ding Zheng, Hsin Chun Hsieh, Chia Chi Lin, Shao Huan Hong, Hsin Chia Tsai, Gene Hsiang Lee, Shih Huang Tung, Cheng Liang Liu, Ming Chou Chen, Antonio Facchetti

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

40 Scopus citations

Abstract

New solution processable 3,5-dithioalkyl dithienothiophene (DSDTT) based small molecular semiconductors end functionalized with various (fused) thiophenes including dithienothiophene (DTT), thienothiophene (TT), and thiophene (T) are synthesized and characterized in organic field effect transistors (OFETs). The new DSDTT core was synthesized via a one-pot [1 + 1 + 1] methodology. For comparison, non-thiolated 3,5-dialkyl dithienothiophene (DRDTT) based molecules are also prepared and characterized. Optical, electrochemical, and computed electronic structures of these molecules are investigated and contrasted. Single crystal data support evidence of S(alkyl)···S(thiophene) intramolecular locks, with a very short intramolecular S-S distance of 3.17 Å, planarizing the structure as for the equivalent extended n-thienoacenes. Via a solution-shearing semiconductor film deposition method, these semiconductors exhibit a OFET hole mobility up to 2.6 cm² V^-1 s^-1, the greatest reported to date for fused/all-thiophene based small molecular organic semiconductors.

Original language	English
Pages (from-to)	1422-1429
Number of pages	8
Journal	Chemistry of Materials
Volume	32
Issue number	4
DOIs	https://doi.org/10.1021/acs.chemmater.9b03967
State	Published - 25 Feb 2020

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10.1021/acs.chemmater.9b03967

CCDC 1906749: Experimental Crystal Structure Determination
Vegiraju, S. (Contributor), Luo, X.-L. (Contributor), Li, L.-H. (Contributor), Afraj, S. N. (Contributor), Lee, C. (Contributor), Zheng, D. (Contributor), Hsieh, H.-C. (Contributor), Lin, C.-C. (Contributor), Hong, S.-H. (Contributor), Tsai, H.-C. (Contributor), Lee, G.-H. (Contributor), Tung, S.-H. (Contributor), Liu, C.-L. (Contributor), Chen, M.-C. (Contributor) & Facchetti, A. (Contributor), Cambridge Crystallographic Data Centre, 2020
DOI: 10.5517/ccdc.csd.cc220419, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc220419&sid=DataCite
Dataset
CCDC 1906747: Experimental Crystal Structure Determination
Vegiraju, S. (Contributor), Luo, X.-L. (Contributor), Li, L.-H. (Contributor), Afraj, S. N. (Contributor), Lee, C. (Contributor), Zheng, D. (Contributor), Hsieh, H.-C. (Contributor), Lin, C.-C. (Contributor), Hong, S.-H. (Contributor), Tsai, H.-C. (Contributor), Lee, G.-H. (Contributor), Tung, S.-H. (Contributor), Liu, C.-L. (Contributor), Chen, M.-C. (Contributor) & Facchetti, A. (Contributor), Cambridge Crystallographic Data Centre, 2020
DOI: 10.5517/ccdc.csd.cc2203z6, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc2203z6&sid=DataCite
Dataset

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Vegiraju, S., Luo, X. L., Li, L. H., Afraj, S. N., Lee, C., Zheng, D., Hsieh, H. C., Lin, C. C., Hong, S. H., Tsai, H. C., Lee, G. H., Tung, S. H., Liu, C. L., Chen, M. C., & Facchetti, A. (2020). Solution Processable Pseudo n-Thienoacenes via Intramolecular S···S Lock for High Performance Organic Field Effect Transistors. Chemistry of Materials, 32(4), 1422-1429. https://doi.org/10.1021/acs.chemmater.9b03967

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title = "Solution Processable Pseudo n-Thienoacenes via Intramolecular S···S Lock for High Performance Organic Field Effect Transistors",

abstract = "New solution processable 3,5-dithioalkyl dithienothiophene (DSDTT) based small molecular semiconductors end functionalized with various (fused) thiophenes including dithienothiophene (DTT), thienothiophene (TT), and thiophene (T) are synthesized and characterized in organic field effect transistors (OFETs). The new DSDTT core was synthesized via a one-pot [1 + 1 + 1] methodology. For comparison, non-thiolated 3,5-dialkyl dithienothiophene (DRDTT) based molecules are also prepared and characterized. Optical, electrochemical, and computed electronic structures of these molecules are investigated and contrasted. Single crystal data support evidence of S(alkyl)···S(thiophene) intramolecular locks, with a very short intramolecular S-S distance of 3.17 {\AA}, planarizing the structure as for the equivalent extended n-thienoacenes. Via a solution-shearing semiconductor film deposition method, these semiconductors exhibit a OFET hole mobility up to 2.6 cm2 V-1 s-1, the greatest reported to date for fused/all-thiophene based small molecular organic semiconductors.",

author = "Sureshraju Vegiraju and Luo, {Xian Lun} and Li, {Long Huan} and Afraj, {Shakil N.} and Chi Lee and Ding Zheng and Hsieh, {Hsin Chun} and Lin, {Chia Chi} and Hong, {Shao Huan} and Tsai, {Hsin Chia} and Lee, {Gene Hsiang} and Tung, {Shih Huang} and Liu, {Cheng Liang} and Chen, {Ming Chou} and Antonio Facchetti",

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doi = "10.1021/acs.chemmater.9b03967",

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Vegiraju, S, Luo, XL, Li, LH, Afraj, SN, Lee, C, Zheng, D, Hsieh, HC, Lin, CC, Hong, SH, Tsai, HC, Lee, GH, Tung, SH, Liu, CL, Chen, MC & Facchetti, A 2020, 'Solution Processable Pseudo n-Thienoacenes via Intramolecular S···S Lock for High Performance Organic Field Effect Transistors', Chemistry of Materials, vol. 32, no. 4, pp. 1422-1429. https://doi.org/10.1021/acs.chemmater.9b03967

TY - JOUR

T1 - Solution Processable Pseudo n-Thienoacenes via Intramolecular S···S Lock for High Performance Organic Field Effect Transistors

AU - Vegiraju, Sureshraju

AU - Luo, Xian Lun

AU - Li, Long Huan

AU - Afraj, Shakil N.

AU - Lee, Chi

AU - Zheng, Ding

AU - Hsieh, Hsin Chun

AU - Lin, Chia Chi

AU - Hong, Shao Huan

AU - Tsai, Hsin Chia

AU - Lee, Gene Hsiang

AU - Tung, Shih Huang

AU - Liu, Cheng Liang

AU - Chen, Ming Chou

AU - Facchetti, Antonio

PY - 2020/2/25

Y1 - 2020/2/25

N2 - New solution processable 3,5-dithioalkyl dithienothiophene (DSDTT) based small molecular semiconductors end functionalized with various (fused) thiophenes including dithienothiophene (DTT), thienothiophene (TT), and thiophene (T) are synthesized and characterized in organic field effect transistors (OFETs). The new DSDTT core was synthesized via a one-pot [1 + 1 + 1] methodology. For comparison, non-thiolated 3,5-dialkyl dithienothiophene (DRDTT) based molecules are also prepared and characterized. Optical, electrochemical, and computed electronic structures of these molecules are investigated and contrasted. Single crystal data support evidence of S(alkyl)···S(thiophene) intramolecular locks, with a very short intramolecular S-S distance of 3.17 Å, planarizing the structure as for the equivalent extended n-thienoacenes. Via a solution-shearing semiconductor film deposition method, these semiconductors exhibit a OFET hole mobility up to 2.6 cm2 V-1 s-1, the greatest reported to date for fused/all-thiophene based small molecular organic semiconductors.

AB - New solution processable 3,5-dithioalkyl dithienothiophene (DSDTT) based small molecular semiconductors end functionalized with various (fused) thiophenes including dithienothiophene (DTT), thienothiophene (TT), and thiophene (T) are synthesized and characterized in organic field effect transistors (OFETs). The new DSDTT core was synthesized via a one-pot [1 + 1 + 1] methodology. For comparison, non-thiolated 3,5-dialkyl dithienothiophene (DRDTT) based molecules are also prepared and characterized. Optical, electrochemical, and computed electronic structures of these molecules are investigated and contrasted. Single crystal data support evidence of S(alkyl)···S(thiophene) intramolecular locks, with a very short intramolecular S-S distance of 3.17 Å, planarizing the structure as for the equivalent extended n-thienoacenes. Via a solution-shearing semiconductor film deposition method, these semiconductors exhibit a OFET hole mobility up to 2.6 cm2 V-1 s-1, the greatest reported to date for fused/all-thiophene based small molecular organic semiconductors.

UR - http://www.scopus.com/inward/record.url?scp=85081707469&partnerID=8YFLogxK

U2 - 10.1021/acs.chemmater.9b03967

DO - 10.1021/acs.chemmater.9b03967

M3 - 期刊論文

AN - SCOPUS:85081707469

SN - 0897-4756

VL - 32

SP - 1422

EP - 1429

JO - Chemistry of Materials

JF - Chemistry of Materials

IS - 4

ER -

Solution Processable Pseudo n-Thienoacenes via Intramolecular S···S Lock for High Performance Organic Field Effect Transistors

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CCDC 1906749: Experimental Crystal Structure Determination

CCDC 1906747: Experimental Crystal Structure Determination

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