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Development of Spiro[cyclopenta[1,2-b:5,4-b']dithiophene-4,9'-fluorene]-Based A-π-D-π-A Small Molecules With Different Acceptor Units for Efficient Organic Solar Cells

Development of Spiro[cyclopenta[1,2-b:5,4-b']dithiophene-4,9'-fluorene]-Based A-π-D-π-A Small Molecules With Different Acceptor Units for Efficient Organic Solar Cells

Wengong Wang, Ping Shen, Xinning Dong, Chao Weng, Guo Wang, Haijun Bin, Jing Zhang, Zhi-Guo Zhang, Yongfang Li

ACS Appl Mater Interfaces. 2017 Feb 8;9(5):4614-4625.

PMID: 28098975

Abstract:

Three acceptor-π-donor-π-acceptor (A-π-D-π-A) small molecules (STFYT, STFRDN, and STFRCN) with spiro[cyclopenta[1,2-b:5,4-b']dithiophene-4,9'-fluorene] (STF) as the central donor unit, terthiophene as the π-conjugated bridge, indenedione, 3-ethylrhodanine, or 2-(1,1-dicyanomethylene)rhodanine as the acceptor unit are designed, synthesized, and characterized as electron donor materials in solution-processing organic solar cells (OSCs). The effects of the spiro STF-based central core and different acceptors on the molecular configuration, absorption properties, electronic energy levels, carrier transport properties, the morphology of active layers, and photovoltaic properties are investigated in detail. The three molecules exhibit desirable physicochemical features: wide absorption bands (300-850 nm) and high molar absorption coefficients (4.82 × 104 to 7.56 × 104 M-1 cm-1) and relatively low HOMO levels (-5.15 to -5.38 eV). Density functional theory calculations reveal that the spiro STF central core benefits to reduce the steric hindrance effect between the central donor block and terthiophene bridge and suppress excessive intermolecular aggregations. The optimized OSCs based on these molecules deliver power conversion efficiencies (PCEs) of 6.68%, 3.30%, and 4.33% for STFYT, STFRDN, and STFRCN, respectively. The higher PCE of STFYT-based OSCs should be ascribed to its better absorption ability, higher and balanced hole and electron mobilities, and superior active layer morphology as compared to the other two compounds. So far, this is the first example of developing the A-π-D-π-A type small molecules with a spiro central donor core for high-performance OSC applications. Meanwhile, these results demonstrate that using spiro central block to construct A-π-D-π-A molecule is an alternative and effective strategy for achieving high-performance small molecule donor materials.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1134942203	2,6-Ditolylbenzo[1,2-b:4,5-b′]dithiophene		1134942-20-3	Price

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