Synthesis of Alternating Donor-Acceptor Ladder-Type Molecules and Investigation of Their Multiple Charge-Transfer Pathways

Zhengxu Cai; Na Zhang; Mohammad A Awais; Alexander S Filatov; Luping Yu

doi:10.1002/anie.201713323

Synthesis of Alternating Donor-Acceptor Ladder-Type Molecules and Investigation of Their Multiple Charge-Transfer Pathways

Angew Chem Int Ed Engl. 2018 May 28;57(22):6442-6448. doi: 10.1002/anie.201713323. Epub 2018 Mar 8.

Authors

Zhengxu Cai¹, Na Zhang¹, Mohammad A Awais¹, Alexander S Filatov¹, Luping Yu¹

Affiliation

¹ Department of Chemistry, The University of Chicago, 929 E 57th Street, Chicago, IL, 60637, USA.

PMID: 29430808
DOI: 10.1002/anie.201713323

Abstract

We describe the synthesis as well as the optical and charge-transport properties of a series of donor-acceptor (D-A) ladder-type heteroacenes. These molecules are stable, soluble, and contain up to 24 fused rings. Structural analyses indicated that the backbones of S 10r and Se 10r are bent in single crystals. The three 10-ring heteroacenes were functionalized with thiol anchoring groups and used for single-molecular conductance measurements. The highest conductance was observed for molecular wires containing a benzoselenadiazole (BSD) moiety, which exhibits the narrowest band gap. Multiple charge-transport pathways were observed in molecular wires containing either benzothiadiazole (BTD) or BSD. The conductance is a complex function of both energy gap and orbital alignment.

Keywords: anchoring groups; donor-acceptor systems; fused-ring systems; molecular electronics; multiple charge-transfer channels.

Publication types

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