Direct C-H arylation for various Ar-cored diketopyrrolopyrrole
containing small molecules in solution-processed field-effect
transistors

J 2016

Direct C-H arylation for various Ar-cored diketopyrrolopyrrole containing small molecules in solution-processed field-effect transistors

WANG, Shifan; JIe YANG; Katharina BROCH; Jiří NOVÁK; Xudong CAO et al.

Základní údaje

Originální název

Direct C-H arylation for various Ar-cored diketopyrrolopyrrole containing small molecules in solution-processed field-effect transistors

Autoři

WANG, Shifan; JIe YANG; Katharina BROCH; Jiří NOVÁK; Xudong CAO; Jessica SHAW; Youtian TAO; Yuanyuan HU a Wei HUANG

Vydání

RSC Advances, Cambridge, Royal Society of Chemistry, 2016, 2046-2069

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10302 Condensed matter physics

Stát vydavatele

Velká Británie a Severní Irsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

Link to the article on the web-page of the publisher

Impakt faktor

Impact factor: 3.108

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14740/16:00092423

Organizační jednotka

Středoevropský technologický institut

Klíčová slova anglicky

diketopyrrolopyrroles; organic semiconductors; electrical properties; x-ray diffraction; organic field effect transitors

Štítky

rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 11. 9. 2018 11:38, Mgr. Jiří Novák, Ph.D.

Anotace

V originále

Direct (hetero) C-H arylation is an advantageous tool for the synthesis of diketopyrrolopyrrole (DPP) derivatives, because of fewer synthetic steps, better atom economy and being environmentally friendly. Herein, four diketopyrrolopyrrole containing linear structured D-A-pi-A-D small molecules Ar(DPPT2)(2) are facilely synthesized in high yields of 73-82% through C-H direct arylation, where Ar (from electron-donating 1,4-phenyl, 1,4-naphthyl or 9,10-anthryl to electron-accepting 2,5-pyridyl) is functionalized as the core pi-bridge structure, DPP as the arm and bithiophene as end-groups. The dihedral angles between the central aryl rings and DPPT2 arms for the optimized geometries of Ph(DPPT2)(2), NA(DPPT2)(2) and AN(DPPT2)(2) gradually increases from 20.3, 44.7 to 93.1 degrees, respectively, which is 18.7 degrees for the pyridyl cored Py(DPPT2)(2). It is found that the optoelectronic properties can be elaborately tuned by variation of the central aryl bridge. Moreover, the coplanarity of the molecules as well as the electronic properties of central Ar units significantly affect the charge transport properties. Ph(DPPT2)(2) possessing the best conjugated backbone planarity exhibits the highest hole mobility of 0.12 cm(2) V-1 s(-1) among the three Ar(DPPT2)(2) compounds based on the electron-donating phenyl, naphthyl and anthryl cores, while the electron-withdrawing pyridyl core Py(DPPT2)(2) shows a poor hole mobility of 6.47 x 10(-4) cm(2) V-1 s(-1) despite of it having the most planar structure.

Návaznosti

LQ1601, projekt VaV

Název: CEITEC 2020 (Akronym: CEITEC2020)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, CEITEC 2020

Citovat

WANG, Shifan; JIe YANG; Katharina BROCH; Jiří NOVÁK; Xudong CAO; Jessica SHAW; Youtian TAO; Yuanyuan HU a Wei HUANG. Direct C-H arylation for various Ar-cored diketopyrrolopyrrole containing small molecules in solution-processed field-effect transistors. RSC Advances. Cambridge: Royal Society of Chemistry, 2016, roč. 6, č. 62, s. "S7163"-"S7173", 11 s. ISSN 2046-2069. Dostupné z: https://doi.org/10.1039/c6ra10832f.

@article{1365463,
   author = {Wang, Shifan and Yang, JIe and Broch, Katharina and Novák, Jiří and Cao, Xudong and Shaw, Jessica and Tao, Youtian and Hu, Yuanyuan and Huang, Wei},
   article_location = {Cambridge},
   article_number = {62},
   doi = {https://doi.org/10.1039/c6ra10832f},
   keywords = {diketopyrrolopyrroles; organic semiconductors; electrical properties; x-ray diffraction; organic field effect transitors},
   language = {eng},
   issn = {2046-2069},
   journal = {RSC Advances},
   title = {Direct C-H arylation for various Ar-cored diketopyrrolopyrrole containing small molecules in solution-processed field-effect transistors},
   url = {http://pubs.rsc.org/en/Content/ArticleLanding/2016/RA/C6RA10832F#!divAbstract},
   volume = {6},
   year = {2016}
}

TY  - JOUR
ID  - 1365463
AU  - Wang, Shifan - Yang, JIe - Broch, Katharina - Novák, Jiří - Cao, Xudong - Shaw, Jessica - Tao, Youtian - Hu, Yuanyuan - Huang, Wei
PY  - 2016
TI  - Direct C-H arylation for various Ar-cored diketopyrrolopyrrole containing small molecules in solution-processed field-effect transistors
JF  - RSC Advances
VL  - 6
IS  - 62
SP  - "S7163"-"S7173"
EP  - "S7163"-"S7173"
PB  - Royal Society of Chemistry
SN  - 20462069
KW  - diketopyrrolopyrroles
KW  - organic semiconductors
KW  - electrical properties
KW  - x-ray diffraction
KW  - organic field effect transitors
UR  - http://pubs.rsc.org/en/Content/ArticleLanding/2016/RA/C6RA10832F#!divAbstract
L2  - http://pubs.rsc.org/en/Content/ArticleLanding/2016/RA/C6RA10832F#!divAbstract
N2  - Direct (hetero) C-H arylation is an advantageous tool for the synthesis of diketopyrrolopyrrole (DPP) derivatives, because of fewer synthetic steps, better atom economy and being environmentally friendly. Herein, four diketopyrrolopyrrole containing linear structured D-A-pi-A-D small molecules Ar(DPPT2)(2) are facilely synthesized in high yields of 73-82% through C-H direct arylation, where Ar (from electron-donating 1,4-phenyl, 1,4-naphthyl or 9,10-anthryl to electron-accepting 2,5-pyridyl) is functionalized as the core pi-bridge structure, DPP as the arm and bithiophene as end-groups. The dihedral angles between the central aryl rings and DPPT2 arms for the optimized geometries of Ph(DPPT2)(2), NA(DPPT2)(2) and AN(DPPT2)(2) gradually increases from 20.3, 44.7 to 93.1 degrees, respectively, which is 18.7 degrees for the pyridyl cored Py(DPPT2)(2). It is found that the optoelectronic properties can be elaborately tuned by variation of the central aryl bridge. Moreover, the coplanarity of the molecules as well as the electronic properties of central Ar units significantly affect the charge transport properties. Ph(DPPT2)(2) possessing the best conjugated backbone planarity exhibits the highest hole mobility of 0.12 cm(2) V-1 s(-1) among the three Ar(DPPT2)(2) compounds based on the electron-donating phenyl, naphthyl and anthryl cores, while the electron-withdrawing pyridyl core Py(DPPT2)(2) shows a poor hole mobility of 6.47 x 10(-4) cm(2) V-1 s(-1) despite of it having the most planar structure.
ER  -

WANG, Shifan; JIe YANG; Katharina BROCH; Jiří NOVÁK; Xudong CAO; Jessica SHAW; Youtian TAO; Yuanyuan HU a Wei HUANG. Direct C-H arylation for various Ar-cored diketopyrrolopyrrole containing small molecules in solution-processed field-effect transistors. \textit{RSC Advances}. Cambridge: Royal Society of Chemistry, 2016, roč.~6, č.~62, s.~''S7163''-''S7173'', 11 s. ISSN~2046-2069. Dostupné z: https://doi.org/10.1039/c6ra10832f.

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