Direct C-H arylation for small molecules composed of diketopyrrolopyrrole and benzothiadiazole as organic semiconductor materials

Shifan Wang; Yuanyuan Hu; Jie Yang; Wei Huang

doi:10.1016/j.synthmet.2019.03.004

Direct C-H arylation for small molecules composed of diketopyrrolopyrrole and benzothiadiazole as organic semiconductor materials

Shifan Wang, Yuanyuan Hu, Jie Yang, Wei Huang

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

8 Scopus citations

Abstract

Direct C-H arylation is an approximate tool for synthesis of thiophene-diketopyrrolopyrrole (DPP) derivatives, because of better atomic economy, fewer synthetic steps and being environmental friendly. In this work, DPP containing linear structured small molecule TBT(DPPT ₂ ) ₂ are facilely synthesized in high yield by the C-H direct arylation, other small molecule TBT(DPP) ₂ are synthesized thought stille cross-crouping reaction. Thermal, optimized geometries, electrochemical, photo-physical properties and film morphology of two materials are studied and solution-coated organic field effect transistors (OFETs) are preparated. TBT(DPPT ₂ ) ₂ have wider band gaps and enhanced electronic defects compare to TBT(DPP) ₂ . Both TBT(DPP) ₂ and TBT(DPPT ₂ ) ₂ demonstrated typical p-type transport with average hole mobility of 1.26 × 10 ⁻³ and 9.58 × 10 ^-4 cm ² V ^-1 s ^-1 respectively.

Original language	English
Pages (from-to)	94-98
Number of pages	5
Journal	Synthetic Metals
Volume	250
DOIs	https://doi.org/10.1016/j.synthmet.2019.03.004
State	Published - Apr 2019
Externally published	Yes

Keywords

Benzothiadiazole
Diketopyrrolopyrrole
Direct C-H arylation
Organic field effect transistors
Organic semiconductor materials

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title = "Direct C-H arylation for small molecules composed of diketopyrrolopyrrole and benzothiadiazole as organic semiconductor materials",

abstract = " Direct C-H arylation is an approximate tool for synthesis of thiophene-diketopyrrolopyrrole (DPP) derivatives, because of better atomic economy, fewer synthetic steps and being environmental friendly. In this work, DPP containing linear structured small molecule TBT(DPPT 2 ) 2 are facilely synthesized in high yield by the C-H direct arylation, other small molecule TBT(DPP) 2 are synthesized thought stille cross-crouping reaction. Thermal, optimized geometries, electrochemical, photo-physical properties and film morphology of two materials are studied and solution-coated organic field effect transistors (OFETs) are preparated. TBT(DPPT 2 ) 2 have wider band gaps and enhanced electronic defects compare to TBT(DPP) 2 . Both TBT(DPP) 2 and TBT(DPPT 2 ) 2 demonstrated typical p-type transport with average hole mobility of 1.26 × 10 −3 and 9.58 × 10 -4 cm 2 V -1 s -1 respectively.",

keywords = "Benzothiadiazole, Diketopyrrolopyrrole, Direct C-H arylation, Organic field effect transistors, Organic semiconductor materials",

author = "Shifan Wang and Yuanyuan Hu and Jie Yang and Wei Huang",

note = "Publisher Copyright: {\textcopyright} 2019",

year = "2019",

month = apr,

doi = "10.1016/j.synthmet.2019.03.004",

language = "英语",

volume = "250",

pages = "94--98",

journal = "Synthetic Metals",

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T1 - Direct C-H arylation for small molecules composed of diketopyrrolopyrrole and benzothiadiazole as organic semiconductor materials

AU - Wang, Shifan

AU - Hu, Yuanyuan

AU - Yang, Jie

AU - Huang, Wei

PY - 2019/4

Y1 - 2019/4

N2 - Direct C-H arylation is an approximate tool for synthesis of thiophene-diketopyrrolopyrrole (DPP) derivatives, because of better atomic economy, fewer synthetic steps and being environmental friendly. In this work, DPP containing linear structured small molecule TBT(DPPT 2 ) 2 are facilely synthesized in high yield by the C-H direct arylation, other small molecule TBT(DPP) 2 are synthesized thought stille cross-crouping reaction. Thermal, optimized geometries, electrochemical, photo-physical properties and film morphology of two materials are studied and solution-coated organic field effect transistors (OFETs) are preparated. TBT(DPPT 2 ) 2 have wider band gaps and enhanced electronic defects compare to TBT(DPP) 2 . Both TBT(DPP) 2 and TBT(DPPT 2 ) 2 demonstrated typical p-type transport with average hole mobility of 1.26 × 10 −3 and 9.58 × 10 -4 cm 2 V -1 s -1 respectively.

AB - Direct C-H arylation is an approximate tool for synthesis of thiophene-diketopyrrolopyrrole (DPP) derivatives, because of better atomic economy, fewer synthetic steps and being environmental friendly. In this work, DPP containing linear structured small molecule TBT(DPPT 2 ) 2 are facilely synthesized in high yield by the C-H direct arylation, other small molecule TBT(DPP) 2 are synthesized thought stille cross-crouping reaction. Thermal, optimized geometries, electrochemical, photo-physical properties and film morphology of two materials are studied and solution-coated organic field effect transistors (OFETs) are preparated. TBT(DPPT 2 ) 2 have wider band gaps and enhanced electronic defects compare to TBT(DPP) 2 . Both TBT(DPP) 2 and TBT(DPPT 2 ) 2 demonstrated typical p-type transport with average hole mobility of 1.26 × 10 −3 and 9.58 × 10 -4 cm 2 V -1 s -1 respectively.

KW - Benzothiadiazole

KW - Diketopyrrolopyrrole

KW - Direct C-H arylation

KW - Organic field effect transistors

KW - Organic semiconductor materials

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U2 - 10.1016/j.synthmet.2019.03.004

DO - 10.1016/j.synthmet.2019.03.004

M3 - 文章

AN - SCOPUS:85062806341

SN - 0379-6779

VL - 250

SP - 94

EP - 98

JO - Synthetic Metals

JF - Synthetic Metals

ER -

Direct C-H arylation for small molecules composed of diketopyrrolopyrrole and benzothiadiazole as organic semiconductor materials

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Keywords

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