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, Jessica SHAW, Youtian TAO, Yuanyuan HU and 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, vol. 6, No 62, p. "S7163"-"S7173", 11 pp. ISSN 2046-2069. Available from: https://dx.doi.org/10.1039/c6ra10832f.

Basic information

• Original name: Direct C-H arylation for various Ar-cored diketopyrrolopyrrole containing small molecules in solution-processed field-effect transistors
• Authors: WANG, Shifan (156 China), JIe YANG (156 China), Katharina BROCH (276 Germany), Jiří NOVÁK (203 Czech Republic, guarantor, belonging to the institution), Xudong CAO (156 China), Jessica SHAW (826 United Kingdom of Great Britain and Northern Ireland), Youtian TAO (156 China), Yuanyuan HU (156 China) and Wei HUANG (156 China).
• Edition: RSC Advances, Cambridge, Royal Society of Chemistry, 2016, 2046-2069.

Other information

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10302 Condensed matter physics
• Country of publisher: United Kingdom of Great Britain and Northern Ireland
• Confidentiality degree: is not subject to a state or trade secret
• WWW: Link to the article on the web-page of the publisher
• Impact factor: Impact factor: 3.108
• RIV identification code: RIV/00216224:14740/16:00092423
• Organization unit: Central European Institute of Technology
• Doi: http://dx.doi.org/10.1039/c6ra10832f
• UT WoS: 000378755200057
• Keywords in English: diketopyrrolopyrroles; organic semiconductors; electrical properties; x-ray diffraction; organic field effect transitors
• Tags: rivok
• Tags: International impact, Reviewed

Abstract

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.

Links

• LQ1601, research and development project: Name: CEITEC 2020 (Acronym: CEITEC2020)

Investor: Ministry of Education, Youth and Sports of the CR