Crystal Engineering of Dibenzothiophenothieno[3,2-b]thiophene (DBTTT) Isomers for Organic Field-Effect Transistors

Hung-Yang Chen; Guillaume Schweicher; Miquel Planells; Sean Ryno; Katharina Broch; Andrew J. P. White; Dimitrios Simatos; Mark Little; Cameron Jellett; Samuel J. Cryer; Adam Marks; Michael Hurhangee; Jean-Luc Bredas; Henning Sirringhaus; Iain McCulloch

doi:10.1021/acs.chemmater.8b02757

Crystal Engineering of Dibenzothiophenothieno[3,2-b]thiophene (DBTTT) Isomers for Organic Field-Effect Transistors

Hung-Yang Chen, Guillaume Schweicher, Miquel Planells, Sean Ryno, Katharina Broch, Andrew J. P. White, Dimitrios Simatos, Mark Little, Cameron Jellett, Samuel J. Cryer, Adam Marks, Michael Hurhangee, Jean-Luc Bredas, Henning Sirringhaus, Iain McCulloch

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

26 Scopus citations

Abstract

Three thiophene ring-terminated benzothieno[3,2-b]benzothiophene (BTBT) derivatives, C-C6-DBTTT, C-C12-DBTTT, and L-C12-DBTTT, were designed and synthesized, differing in the isomerization of alkyl chain position as well as aromatic core construction. A study of crystal structure and electronic properties combined with a theoretical investigation was performed to understand the structure-property relationships for the application of these molecules in organic field-effect transistors (OFETs). Different crystal packing structures were observed for these three isomers by single-crystal X-ray diffraction as a result of a crystal engineering molecular design approach. The highest charge-carrier mobility was observed for the isomer with a collinear core, L-C12-DBTTT. Preliminary results demonstrated a promising hole mobility of 2.44 cm V s, despite the polymorphism observed in ambient conditions.

Original language	English (US)
Pages (from-to)	7587-7592
Number of pages	6
Journal	Chemistry of Materials
Volume	30
Issue number	21
DOIs	https://doi.org/10.1021/acs.chemmater.8b02757
State	Published - Oct 25 2018

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10.1021/acs.chemmater.8b02757

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Chen, H.-Y., Schweicher, G., Planells, M., Ryno, S., Broch, K., White, A. J. P., Simatos, D., Little, M., Jellett, C., Cryer, S. J., Marks, A., Hurhangee, M., Bredas, J.-L., Sirringhaus, H., & McCulloch, I. (2018). Crystal Engineering of Dibenzothiophenothieno[3,2-b]thiophene (DBTTT) Isomers for Organic Field-Effect Transistors. Chemistry of Materials, 30(21), 7587-7592. https://doi.org/10.1021/acs.chemmater.8b02757

@article{5182b8d5d4e044cf80034bdf5bd64f5d,

title = "Crystal Engineering of Dibenzothiophenothieno[3,2-b]thiophene (DBTTT) Isomers for Organic Field-Effect Transistors",

abstract = "Three thiophene ring-terminated benzothieno[3,2-b]benzothiophene (BTBT) derivatives, C-C6-DBTTT, C-C12-DBTTT, and L-C12-DBTTT, were designed and synthesized, differing in the isomerization of alkyl chain position as well as aromatic core construction. A study of crystal structure and electronic properties combined with a theoretical investigation was performed to understand the structure-property relationships for the application of these molecules in organic field-effect transistors (OFETs). Different crystal packing structures were observed for these three isomers by single-crystal X-ray diffraction as a result of a crystal engineering molecular design approach. The highest charge-carrier mobility was observed for the isomer with a collinear core, L-C12-DBTTT. Preliminary results demonstrated a promising hole mobility of 2.44 cm V s, despite the polymorphism observed in ambient conditions.",

author = "Hung-Yang Chen and Guillaume Schweicher and Miquel Planells and Sean Ryno and Katharina Broch and White, {Andrew J. P.} and Dimitrios Simatos and Mark Little and Cameron Jellett and Cryer, {Samuel J.} and Adam Marks and Michael Hurhangee and Jean-Luc Bredas and Henning Sirringhaus and Iain McCulloch",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: H.-Y.C. acknowledges postdoctoral fellowship support from Ministry of Science and Technology in Taiwan. G.S. acknowledges postdoctoral fellowship support from the Wiener-Anspach Foundation and The Leverhulme Trust (Early Career Fellowship supported by the Isaac Newton Trust). We acknowledge the European Synchrotron Radiation Facility for provision of synchrotron radiation facilities, and we thank Dr. Raja Znaiguia and Dr. Francesco Carla for assistance in using beamline ID03. K.B. acknowledges financial support from the Institutional Strategy of the University of Tuebingen (Deutsche Forschungsgemeinschaft ZUK63). I.M., S.C., C.J., and M.L. acknowledge EC FP7 SC2 (610115), EC H2020 (643791), and EPSRC Projects EP/G037515/1 EP/M024873/1 and EP/M005143/1.",

year = "2018",

month = oct,

day = "25",

doi = "10.1021/acs.chemmater.8b02757",

language = "English (US)",

volume = "30",

pages = "7587--7592",

journal = "Chemistry of Materials",

issn = "0897-4756",

publisher = "American Chemical Society",

number = "21",

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Chen, H-Y, Schweicher, G, Planells, M, Ryno, S, Broch, K, White, AJP, Simatos, D, Little, M, Jellett, C, Cryer, SJ, Marks, A, Hurhangee, M, Bredas, J-L, Sirringhaus, H & McCulloch, I 2018, 'Crystal Engineering of Dibenzothiophenothieno[3,2-b]thiophene (DBTTT) Isomers for Organic Field-Effect Transistors', Chemistry of Materials, vol. 30, no. 21, pp. 7587-7592. https://doi.org/10.1021/acs.chemmater.8b02757

TY - JOUR

T1 - Crystal Engineering of Dibenzothiophenothieno[3,2-b]thiophene (DBTTT) Isomers for Organic Field-Effect Transistors

AU - Chen, Hung-Yang

AU - Schweicher, Guillaume

AU - Planells, Miquel

AU - Ryno, Sean

AU - Broch, Katharina

AU - White, Andrew J. P.

AU - Simatos, Dimitrios

AU - Little, Mark

AU - Jellett, Cameron

AU - Cryer, Samuel J.

AU - Marks, Adam

AU - Hurhangee, Michael

AU - Bredas, Jean-Luc

AU - Sirringhaus, Henning

AU - McCulloch, Iain

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: H.-Y.C. acknowledges postdoctoral fellowship support from Ministry of Science and Technology in Taiwan. G.S. acknowledges postdoctoral fellowship support from the Wiener-Anspach Foundation and The Leverhulme Trust (Early Career Fellowship supported by the Isaac Newton Trust). We acknowledge the European Synchrotron Radiation Facility for provision of synchrotron radiation facilities, and we thank Dr. Raja Znaiguia and Dr. Francesco Carla for assistance in using beamline ID03. K.B. acknowledges financial support from the Institutional Strategy of the University of Tuebingen (Deutsche Forschungsgemeinschaft ZUK63). I.M., S.C., C.J., and M.L. acknowledge EC FP7 SC2 (610115), EC H2020 (643791), and EPSRC Projects EP/G037515/1 EP/M024873/1 and EP/M005143/1.

PY - 2018/10/25

Y1 - 2018/10/25

N2 - Three thiophene ring-terminated benzothieno[3,2-b]benzothiophene (BTBT) derivatives, C-C6-DBTTT, C-C12-DBTTT, and L-C12-DBTTT, were designed and synthesized, differing in the isomerization of alkyl chain position as well as aromatic core construction. A study of crystal structure and electronic properties combined with a theoretical investigation was performed to understand the structure-property relationships for the application of these molecules in organic field-effect transistors (OFETs). Different crystal packing structures were observed for these three isomers by single-crystal X-ray diffraction as a result of a crystal engineering molecular design approach. The highest charge-carrier mobility was observed for the isomer with a collinear core, L-C12-DBTTT. Preliminary results demonstrated a promising hole mobility of 2.44 cm V s, despite the polymorphism observed in ambient conditions.

AB - Three thiophene ring-terminated benzothieno[3,2-b]benzothiophene (BTBT) derivatives, C-C6-DBTTT, C-C12-DBTTT, and L-C12-DBTTT, were designed and synthesized, differing in the isomerization of alkyl chain position as well as aromatic core construction. A study of crystal structure and electronic properties combined with a theoretical investigation was performed to understand the structure-property relationships for the application of these molecules in organic field-effect transistors (OFETs). Different crystal packing structures were observed for these three isomers by single-crystal X-ray diffraction as a result of a crystal engineering molecular design approach. The highest charge-carrier mobility was observed for the isomer with a collinear core, L-C12-DBTTT. Preliminary results demonstrated a promising hole mobility of 2.44 cm V s, despite the polymorphism observed in ambient conditions.

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UR - https://pubs.acs.org/doi/10.1021/acs.chemmater.8b02757

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U2 - 10.1021/acs.chemmater.8b02757

DO - 10.1021/acs.chemmater.8b02757

M3 - Article

SN - 0897-4756

VL - 30

SP - 7587

EP - 7592

JO - Chemistry of Materials

JF - Chemistry of Materials

IS - 21

ER -

Crystal Engineering of Dibenzothiophenothieno[3,2-b]thiophene (DBTTT) Isomers for Organic Field-Effect Transistors

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CCDC 1590308: Experimental Crystal Structure Determination : 2,8-didodecylthieno[3',2':5,6][1]benzothieno[3,2-b]thieno[3,2-f][1]benzothiophene

CCDC 1590306: Experimental Crystal Structure Determination : 4,5,10,11-tetrahexylthieno[3',2':6,7][1]benzothieno[3,2-b]thieno[3,2-g][1]benzothiophene

CCDC 1590307: Experimental Crystal Structure Determination : 2,8-didodecylthieno[3',2':6,7][1]benzothieno[3,2-b]thieno[3,2-g][1]benzothiophene

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Crystal Engineering of Dibenzothiophenothieno[3,2-b]thiophene (DBTTT) Isomers for Organic Field-Effect Transistors

Abstract

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Datasets

CCDC 1590308: Experimental Crystal Structure Determination : 2,8-didodecylthieno[3',2':5,6][1]benzothieno[3,2-b]thieno[3,2-f][1]benzothiophene

CCDC 1590306: Experimental Crystal Structure Determination : 4,5,10,11-tetrahexylthieno[3',2':6,7][1]benzothieno[3,2-b]thieno[3,2-g][1]benzothiophene

CCDC 1590307: Experimental Crystal Structure Determination : 2,8-didodecylthieno[3',2':6,7][1]benzothieno[3,2-b]thieno[3,2-g][1]benzothiophene

Cite this