Abstract
Two novel aromatic imides, diarylcyclopentadienone-fused naphthalimides (BCPONI-2Br and TCPONI-2Br), are designed and synthesized by condensation coupling cyclopentadienone derivatives at the lateral position of naphthalimide skeleton. It has been found that BCPONI-2Br and TCPONI-2Br are highly electron-withdrawing acceptor moieties, which possess broad absorption bands and very low-lying LUMO energy levels, as low as −4.02 eV. On the basis of both building blocks, six low bandgap D-A copolymers (P1–P6) are prepared via Suzuki or Stille coupling reactions. The optical and electrochemical properties of the polymers are fine-tuned by the variations of donors (carbazole, benzodithiophene, and dithienopyrrole) and π-conjugation linkers (thiophene and benzene). All polymers exhibit several attractive photophysical and electrochemical properties, i.e., broad near-infrared (NIR) absorption, deep-lying LUMO levels (between −3.88 and −3.76 eV), and a very small optical bandgap as low as 0.81 eV, which represents the first aromatic diimide-based polymer with an of <1.0 eV. An investigation of charge carrier transport properties shows that P5 exhibits a moderately high hole mobility of 0.02 cm2 V−1 s−1 in bottom-gate field-effect transistors (FETs) and a typical ambipolar transport behavior in top-gate FETs. The findings suggest that BCPONI-2Br, TCPONI-2Br, and the other similar acceptor units are promising building blocks for novel organic semiconductors with outstanding NIR activity, high electron affinity, and low bandgap, which can be extended to various next-generation optoelectronic devices.
Highlights
Zhan and co-workers reported the synthesis of the first soluble PDIdithienothiophene copolymers (Zhan et al, 2007), which yielded a moderately high electron mobility of 0.013 cm2 V−1 s−1 and a power conversion efficiency (PCE) value of 1.5% when used as the active layers in topgate organic field-effect transistors (OFETs) and all-polymer organic photovoltaicsLow Bandgap Donor-Acceptor π-Conjugated Polymers (OPVs), respectively
The findings presented above suggest that BCPONI-2Br and TCPONI-2Br are promising building blocks for the construction of polymer electron-transporting materials with attractive electronic properties
We have designed and synthesized two novel aromatic imides, diarylcyclopentadienone-fused naphthalimides (BCPONI-2Br and TCPONI-2Br), in which a five-membered cyclopentadienone unit is fused at the lateral position of the naphthalimide skeleton
Summary
Soluble donor–acceptor (D–A) conjugated polymers can offer a flexible and tunable electronic structure and optoelectronic properties (Guo et al, 2014; Dou et al, 2015), which encourage the incessant exploration of multiple potential applications in next-generation optoelectronic devices, including organic light-emitting diodes (OLEDs) (Grimsdale et al, 2009), organic photovoltaicsLow Bandgap Donor-Acceptor π-Conjugated Polymers (OPVs) (Cheng et al, 2009), organic field-effect transistors (OFETs) (Hu et al, 2018; Yang et al, 2018), and organic photodetectors (OPDs) (Gong et al, 2009). A mixture of BCPONI-2Br (147 mg, 0.16 mmol), 2,6-bis(trimethyltin)-4,8-di(2-hexyl)decyloxybenzo[1,2b;3,4-b′]dithiophene (177 mg, 0.16 mmol), Pd2(dba)3 (9 mg), P(o-tol)3 (15 mg), and anhydrous chlorobenzene (5 mL) was added into a 25 mL Schlenk tube. A mixture of BCPONI-2Br (147 mg, 0.16 mmol), 2,6bis(trimethylstannyl)-N-(2-decyltetradecyl)-dithieno[3,2b:2′,3′-d]pyrrole (135 mg, 0.16 mmol), Pd2(dba)3 (9 mg), P(o-tol)3 (15 mg), and anhydrous chlorobenzene (5 mL) was added to a 25 mL Schlenk tube.
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
