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1.
J Am Chem Soc ; 146(1): 833-848, 2024 Jan 10.
Artigo em Inglês | MEDLINE | ID: mdl-38113458

RESUMO

The high-performance Y6-based nonfullerene acceptors (NFAs) feature a C-shaped A-DA'D-A-type molecular architecture with a central electron-deficient thiadiazole (Tz) A' unit. In this work, we designed and synthesized a new A-D-A-type NFA, termed CB16, having a C-shaped ortho-benzodipyrrole-based skeleton of Y6 but with the Tz unit eliminated. When processed with nonhalogenated xylene without using any additives, the binary PM6:CB16 devices display a remarkable power conversion efficiency (PCE) of 18.32% with a high open-circuit voltage (Voc) of 0.92 V, surpassing the performance of the corresponding Y6-based devices. In contrast, similarly synthesized SB16, featuring an S-shaped para-benzodipyrrole-based skeleton, yields a low PCE of 0.15% due to the strong side-chain aggregation of SB16. The C-shaped A-DNBND-A skeleton in CB16 and the Y6-series NFAs constitutes the essential structural foundation for achieving exceptional device performance. The central Tz moiety or other A' units can be employed to finely adjust intermolecular interactions. The single-crystal X-ray structure reveals that ortho-benzodipyrrole-embedded A-DNBND-A plays an important role in the formation of a 3D elliptical network packing for efficient charge transport. Solution structures of the PM6:NFAs detected by small- and wide-angle X-ray scattering (SWAXS) indicate that removing the Tz unit in the C-shaped skeleton could reduce the self-packing of CB16, thereby enhancing the complexing and networking with PM6 in the spin-coating solution and the subsequent device film. Elucidating the structure-property-performance relationships of A-DA'D-A-type NFAs in this work paves the way for the future development of structurally simplified A-D-A-type NFAs.

2.
Chem Sci ; 14(32): 8552-8563, 2023 Aug 16.
Artigo em Inglês | MEDLINE | ID: mdl-37592995

RESUMO

Sequence-controlled polychalcogenophenes have attracted much interest in terms of synthesis, structure and function in polymer science. For the first time, we developed a new class of alternating block conjugated copolymers denoted as poly(alt-AB)x-b-(alt-AC)y where both blocks are constituted by an alternating copolymer. 3-Hexylthiophene (S), 3-hexylselenophene (Se) and 3-hexyltellurophene (Te) are used as A, B and C units to assemble three sequence-controlled polychalcogenophenes P(SSe)b(STe), P(SSe)b(SeTe) and P(STe)b(SeTe) which are prepared by adding two different Grignard monomers in sequence to carry out Ni(dppp)Cl2-catalyzed Kumada polymerization. The molecular weight, dispersity, and length of each block (x = y) and main-chain sequence can be synthetically controlled via the catalyst transfer polycondensation mechanism. The polymer structures, i.e. alternating block main chain with high side-chain regioregularity, are unambiguously confirmed by 1H-NMR and 13C-NMR. The optical and electrochemical properties of the polymers can be systematically fine-tuned by the composition and ratio of the chalcogenophenes. From GIWAXS measurements, all the polymers exhibited predominantly edge-on orientations, indicating that the packing behaviors of the alternating block polychalcogenophenes with high regioregularity are inherited from the highly crystalline P3HT. P(SSe)b(STe) exhibited a hole OFET mobility of 1.4 × 10-2 cm2 V-1 s-1, which represents one of the highest values among the tellurophene-containing polychalcogenophenes. The tellurophene units in the polymers can undergo Br2 addition to form the oxidized TeBr2 species which results in dramatically red-shifted absorption due to the alternating arrangement to induce strong charge transfer character. The OFET devices using the tellurophene-containing polychalcogenophenes can be applied for Br2 detection, showing high sensitivity, selectivity and reversibility.

3.
ACS Appl Mater Interfaces ; 11(36): 33179-33187, 2019 Sep 11.
Artigo em Inglês | MEDLINE | ID: mdl-31416309

RESUMO

Benzene-based 1,1-dicyanomethylene-3-indanone (IC) derivatives have been widely utilized as the end-group to construct acceptor-donor-acceptor type nonfullerene acceptors (A-D-A type NFAs). The extension of the end-group conjugation of nonfullerene acceptors (NFAs) is a rational strategy to facilitate intermolecular stacking of the end-groups which are responsible for efficient electron transportation. A bicyclic benzothiophene-based end-group acceptor, 2-(3-oxo-2,3-dihydro-1H-benzo[b]cyclopenta[d]thiophen-1-ylidene)malononitrile, denoted as α-BC was designed and synthesized. The Knoevenagel condensation of the unsymmetrical 1,3-diketo-precursor with one equivalent of malononitrile selectively reacts with the keto group attached at the α-position of the thiophene unit, leading to the isomerically pure benzothiophene-fused α-BC. The well-defined α-BC with extended conjugation was condensed with three different ladder-type diformylated donors to form three new A-D-A NFAs named BDCPDT-BC, DTCC-BC, and ITBC, respectively. The corresponding IC-based BDCPDT-IC, DTCC-IC, and ITIC model compounds were also synthesized for comparison. The incorporation of the electron-rich benzothiophene unit in the end-group upshifts the lowest unoccupied molecular orbital energy levels of the NFAs, which beneficially enlarges the Voc values. On the other hand, the benzothiophene unit in α-BC not also imparts an optical transition in the shorter wavelengths around 340-400 nm for a better light harvesting ability but also promotes the antiparallel π-π stacking of the end-groups for efficient electron transport. The organic photovoltaic cell devices using a PBDB-T polymer and BC-based NFAs all showed the improved Voc and Jsc values. The BDCPDT-BC- and DTCC-BC-based devices exhibited a power conversion efficiency (PCE) of 10.82 and 10.74%, respectively, which outperformed the corresponding BDCPDT-IC-, and DTCC-IC-based devices (9.33 and 9.25%). More importantly, the ITBC-based device delivered the highest PCE of 12.07% with a Jsc of 19.90 mA/cm2, a Voc of 0.94 V, and an fill factor of 64.51%, representing a 14% improvement relative to the traditional ITIC-based device (10.05%).

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