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Synthesis of Alternating Donor–Acceptor Ladder‐Type Molecules and Investigation of Their Multiple Charge‐Transfer Pathways
Author(s) -
Cai Zhengxu,
Zhang Na,
Awais Mohammad A.,
Filatov Alexander S.,
Yu Luping
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201713323
Subject(s) - conductance , moiety , acceptor , molecule , chemistry , charge (physics) , molecular orbital , crystallography , ring (chemistry) , band gap , bent molecular geometry , molecular wire , charge transfer complex , stereochemistry , materials science , photochemistry , organic chemistry , optoelectronics , condensed matter physics , physics , quantum mechanics
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.