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

30 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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10.1021/acs.chemmater.8b02757

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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

@article{9c882c86673e4502a27dc98cb100c1af,

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)",

volume = "30",

pages = "7587--7592",

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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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SP - 7587

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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

Abstract

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