Large π-Conjugated Quinacridone Derivatives: Syntheses, Characterizations, Emission, and Charge Transport Properties

Weiping Chen; Kui Tian; Xiaoxian Song; Zuolun Zhang; Kaiqi Ye; Gui Yu; Yue Wang

doi:10.1021/acs.orglett.5b03155

Large π-Conjugated Quinacridone Derivatives: Syntheses, Characterizations, Emission, and Charge Transport Properties

Org Lett. 2015 Dec 18;17(24):6146-9. doi: 10.1021/acs.orglett.5b03155. Epub 2015 Nov 25.

Authors

Weiping Chen¹, Kui Tian², Xiaoxian Song¹, Zuolun Zhang¹, Kaiqi Ye¹, Gui Yu², Yue Wang¹

Affiliations

¹ State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University , Changchun 130012, China.
² Beijing National Laboratory of Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences , Beijing 100190, China.

PMID: 26605431
DOI: 10.1021/acs.orglett.5b03155

Abstract

Two 11-ring-fused quinacridone derivatives, TTQA and DCNTTQA, have been synthesized by ferric chloride mediated cyclization and Knoevenagel reaction. Replacement of the carbonyl groups (in TTQA) with dicyanoethylene groups (in DCNTTQA) not only red-shifted the emission to the near-infrared region but also led to a nonplanar skeleton that significantly improved the solubility of DCNTTQA. Moreover, dicyanoethylene groups rendered DCNTTQA low-lying HOMO and LUMO levels. DCNTTQA-based solution-processed field-effect transistors showed a hole mobility up to 0.217 cm(2) V(-1) s(-1).

Publication types

Research Support, Non-U.S. Gov't