Dithiophene-Fused Tetracyanonaphthoquinodimethanes (DT-TNAPs): synthesis and characterization of π-extended quinoidal compounds for n-channel organic semiconductor

Naoyuki Yanai; Takamichi Mori; Shoji Shinamura; Itaru Osaka; Kazuo Takimiya

doi:10.1021/ol403234q

Dithiophene-Fused Tetracyanonaphthoquinodimethanes (DT-TNAPs): synthesis and characterization of π-extended quinoidal compounds for n-channel organic semiconductor

Org Lett. 2014 Jan 3;16(1):240-3. doi: 10.1021/ol403234q. Epub 2013 Dec 12.

Authors

Naoyuki Yanai¹, Takamichi Mori, Shoji Shinamura, Itaru Osaka, Kazuo Takimiya

Affiliation

¹ Emergent Molecular Function Research Group, RIKEN Center for Emergent Matter Science (CEMS) , Wako, Saitama 351-0198, Japan.

PMID: 24328863
DOI: 10.1021/ol403234q

Abstract

Dithiophene-fused tetracyanonaphthoquinodimethanes (DTTNAPs) were synthesized and evaluated as n-channel organic semiconductors. DTTNAPs, regardless of isomeric structures and substituents, have low-lying LUMO energy levels (∼4.6 eV below the vacuum level), suitable for stable n-channel field-effect transistors (FETs) under ambient conditions. In fact, α-DTTNAP derivatives afforded solution-processed FETs showing an electron mobility of 10(-3) cm(2) V(-1) s(-1), indicating that DTTNAPs are a potential molecular framework for n-channel organic semiconductors.