Enantiopure versus racemic naphthalene diimide-based n-type organic semiconductors: effect on charge transport

Ming Chen, Jing Li, Xuechen Jiao, Xiaochun Yang, Wenting Wu, Christopher R. McNeill, Xike Gao

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Chiral alkyl chains are widely utilized to ensure the solubility of solution-processed organic semiconductors (OSCs), while intrinsic defects due to the mixture of several stereoisomers in one material are frequently neglected. Herein, through introducing an optically pure pendant into the molecular backbone of a core-expanded naphthalene diimide (NDI-DTYM2), enantiopure semiconductor materials (1-R/1-S) and the corresponding racemate (1-rac) were designed and synthesized to investigate the impact of enantiopure and racemic OSCs on charge transport in organic field-effect transistors (OFETs). Surprisingly, a 2-4 times increase in electron mobility (from 0.15 cm2 V-1 s-1 to 0.6 cm2 V-1 s-1 for as-cast devices and from 0.42 cm2 V-1 s-1 to 0.98 cm2 V-1 s-1 for thermally-annealed devices) was discovered in solution-processed OFETs simply by switching the active layer material from racemic to the enantiopure form. Grazing-incidence wide-angle X-ray scattering (GIWAXS), atomic force microscopy (AFM) and were utilized to investigate the crystallization, molecular micro-organization and film morphology of 1-R, 1-S and 1-rac, demonstrating that the lower mobility of racemic material (1-rac) might be attributed to interfacial defects among different crystalline domains as well as subtle changes in molecular packing.

Original languageEnglish
Pages (from-to)2659-2665
Number of pages7
JournalJournal of Materials Chemistry C
Volume7
Issue number9
DOIs
Publication statusPublished - 1 Jan 2019

Cite this

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title = "Enantiopure versus racemic naphthalene diimide-based n-type organic semiconductors: effect on charge transport",
abstract = "Chiral alkyl chains are widely utilized to ensure the solubility of solution-processed organic semiconductors (OSCs), while intrinsic defects due to the mixture of several stereoisomers in one material are frequently neglected. Herein, through introducing an optically pure pendant into the molecular backbone of a core-expanded naphthalene diimide (NDI-DTYM2), enantiopure semiconductor materials (1-R/1-S) and the corresponding racemate (1-rac) were designed and synthesized to investigate the impact of enantiopure and racemic OSCs on charge transport in organic field-effect transistors (OFETs). Surprisingly, a 2-4 times increase in electron mobility (from 0.15 cm2 V-1 s-1 to 0.6 cm2 V-1 s-1 for as-cast devices and from 0.42 cm2 V-1 s-1 to 0.98 cm2 V-1 s-1 for thermally-annealed devices) was discovered in solution-processed OFETs simply by switching the active layer material from racemic to the enantiopure form. Grazing-incidence wide-angle X-ray scattering (GIWAXS), atomic force microscopy (AFM) and were utilized to investigate the crystallization, molecular micro-organization and film morphology of 1-R, 1-S and 1-rac, demonstrating that the lower mobility of racemic material (1-rac) might be attributed to interfacial defects among different crystalline domains as well as subtle changes in molecular packing.",
author = "Ming Chen and Jing Li and Xuechen Jiao and Xiaochun Yang and Wenting Wu and McNeill, {Christopher R.} and Xike Gao",
year = "2019",
month = "1",
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doi = "10.1039/c8tc06273k",
language = "English",
volume = "7",
pages = "2659--2665",
journal = "Journal of Materials Chemistry C",
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publisher = "The Royal Society of Chemistry",
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Enantiopure versus racemic naphthalene diimide-based n-type organic semiconductors : effect on charge transport. / Chen, Ming; Li, Jing; Jiao, Xuechen; Yang, Xiaochun; Wu, Wenting; McNeill, Christopher R.; Gao, Xike.

In: Journal of Materials Chemistry C, Vol. 7, No. 9, 01.01.2019, p. 2659-2665.

Research output: Contribution to journalArticleResearchpeer-review

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T1 - Enantiopure versus racemic naphthalene diimide-based n-type organic semiconductors

T2 - effect on charge transport

AU - Chen, Ming

AU - Li, Jing

AU - Jiao, Xuechen

AU - Yang, Xiaochun

AU - Wu, Wenting

AU - McNeill, Christopher R.

AU - Gao, Xike

PY - 2019/1/1

Y1 - 2019/1/1

N2 - Chiral alkyl chains are widely utilized to ensure the solubility of solution-processed organic semiconductors (OSCs), while intrinsic defects due to the mixture of several stereoisomers in one material are frequently neglected. Herein, through introducing an optically pure pendant into the molecular backbone of a core-expanded naphthalene diimide (NDI-DTYM2), enantiopure semiconductor materials (1-R/1-S) and the corresponding racemate (1-rac) were designed and synthesized to investigate the impact of enantiopure and racemic OSCs on charge transport in organic field-effect transistors (OFETs). Surprisingly, a 2-4 times increase in electron mobility (from 0.15 cm2 V-1 s-1 to 0.6 cm2 V-1 s-1 for as-cast devices and from 0.42 cm2 V-1 s-1 to 0.98 cm2 V-1 s-1 for thermally-annealed devices) was discovered in solution-processed OFETs simply by switching the active layer material from racemic to the enantiopure form. Grazing-incidence wide-angle X-ray scattering (GIWAXS), atomic force microscopy (AFM) and were utilized to investigate the crystallization, molecular micro-organization and film morphology of 1-R, 1-S and 1-rac, demonstrating that the lower mobility of racemic material (1-rac) might be attributed to interfacial defects among different crystalline domains as well as subtle changes in molecular packing.

AB - Chiral alkyl chains are widely utilized to ensure the solubility of solution-processed organic semiconductors (OSCs), while intrinsic defects due to the mixture of several stereoisomers in one material are frequently neglected. Herein, through introducing an optically pure pendant into the molecular backbone of a core-expanded naphthalene diimide (NDI-DTYM2), enantiopure semiconductor materials (1-R/1-S) and the corresponding racemate (1-rac) were designed and synthesized to investigate the impact of enantiopure and racemic OSCs on charge transport in organic field-effect transistors (OFETs). Surprisingly, a 2-4 times increase in electron mobility (from 0.15 cm2 V-1 s-1 to 0.6 cm2 V-1 s-1 for as-cast devices and from 0.42 cm2 V-1 s-1 to 0.98 cm2 V-1 s-1 for thermally-annealed devices) was discovered in solution-processed OFETs simply by switching the active layer material from racemic to the enantiopure form. Grazing-incidence wide-angle X-ray scattering (GIWAXS), atomic force microscopy (AFM) and were utilized to investigate the crystallization, molecular micro-organization and film morphology of 1-R, 1-S and 1-rac, demonstrating that the lower mobility of racemic material (1-rac) might be attributed to interfacial defects among different crystalline domains as well as subtle changes in molecular packing.

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SN - 2050-7526

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