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

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

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

24 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 cm² V^-1 s^-1, 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 - Nov 13 2018
Externally published	Yes

All Science Journal Classification (ASJC) codes

General Chemistry
General Chemical Engineering
Materials Chemistry

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Chen, H. Y., Schweicher, G., Planells, M., Ryno, S. M., Broch, K., White, A. J. P., Simatos, D., Little, M., Jellett, C., Cryer, S. J., Marks, A., Hurhangee, M., Brédas, 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

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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 cm2 V-1 s-1, despite the polymorphism observed in ambient conditions.",

author = "Chen, {Hung Yang} and Guillaume Schweicher and Miquel Planells and Ryno, {Sean M.} 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 Br{\'e}das, {Jean Luc} and Henning Sirringhaus and Iain McCulloch",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = nov,

day = "13",

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

language = "English (US)",

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Chen, HY, Schweicher, G, Planells, M, Ryno, SM, Broch, K, White, AJP, Simatos, D, Little, M, Jellett, C, Cryer, SJ, Marks, A, Hurhangee, M, Brédas, JL, 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 M.

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 - Brédas, Jean Luc

AU - Sirringhaus, Henning

AU - McCulloch, Iain

PY - 2018/11/13

Y1 - 2018/11/13

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 cm2 V-1 s-1, 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 cm2 V-1 s-1, despite the polymorphism observed in ambient conditions.

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

Abstract

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