A Novel Bis-Lactam Acceptor with Outstanding Molar Extinction Coefficient and Structural Planarity for Donor–Acceptor Type Conjugated Polymer

A novel electron-accepting
bis-lactam building block, 3,7-dithiophen-2-yl-1,5-dialkyl-1,5-naphthyridine-2,6-dione
(NTDT), and a conjugated polymer P­(NTDT-BDT) comprising NTDT as an
electron acceptor and benzo­[1,2-b:4,5-b′]­dithiophene (BDT) as an electron donor are designed and
synthesized for producing efficient organic solar cells. The thermal,
electronic, photophysical, electrochemical, and structural characteristics
of NTDT and P­(NTDT-BDT) are studied in detail and compared with those
of the widely used bis-lactam acceptor 3,6-dithiophen-2-yl-2,5-dialkylpyrrolo­[3,4-c]­pyrrole-1,4-dione (DPPT) and its polymer P­(DPPT-BDT).
Compared to DPPT derivatives, NTDT and P­(NTDT-BDT) exhibit remarkably
higher absorption coefficients, deeper highest occupied molecular
orbital energy levels, and more planar conformations. A bulk heterojunction
solar cells based on P­(NTDT-BDT) exhibit power conversion efficiency
of up to 8.16% with high short circuit current (Jsc) of 18.51 mA cm–2, one of the highest Jsc values yet obtained for BDT-based polymer.
Thus, it is successfully demonstrated that the novel bis-lactam unit
NTDT is a promising building block for use in organic photovoltaic
devices.