Isomeric Small Molecule Donor with Terminal Branching Position Directly Attached to the Backbone Enables Efficient All-Small-Molecule Organic Solar Cells with Excellent Stability

Hong Fu Zhi; Mengyun Jiang; Heng Zhang; Qiaoshi An; Hai Rui Bai; Min Hun Jee; Han Young Woo; Danwei Li; Xuebin Huang; Jin Liang Wang

doi:10.1002/adfm.202300878

Isomeric Small Molecule Donor with Terminal Branching Position Directly Attached to the Backbone Enables Efficient All-Small-Molecule Organic Solar Cells with Excellent Stability

Hong Fu Zhi, Mengyun Jiang, Heng Zhang, Qiaoshi An, Hai Rui Bai, Min Hun Jee, Han Young Woo, Danwei Li, Xuebin Huang, Jin Liang Wang

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

All-small-molecule organic solar cells (ASM-OSCs) are challenging for their inadequate efficiency and device stability due to their more susceptive morphology. Herein, a family of isomeric small molecule donors (SMDs) is synthesized based on the benzodithiophene–terthiophene core with linear, 1st carbon, and 2nd carbon position branched butyl-based rhodanine for ASM-OSCs, respectively. The single crystal of thiophene-substituted model T-s-Bu forms a more compact intermolecular packing with herringbone structure than slip-layered packing-based T-n-Bu and T-i-Bu. SM-i-Bu and SM-s-Bu show slightly blue-shifted absorption and deepened HOMO levels in the neat film compared to SM-n-Bu. SM-s-Bu:BO-4Cl blend films have distinct face-on packing orientations and suitable fibrous phase separation along with more apparent microcrystals. Finally, SM-s-Bu:BO-4Cl-based device yields an improved power conversion efficiency of 16.06% compared to 15.12% and 8.22% for SM-n-Bu:BO-4Cl and SM-i-Bu:BO-4Cl, which is one of the top-ranked results for BTR-series SMDs in binary ASM-OSCs. More importantly, the excellent storage stability with a T₈₀ lifetime of over 1700 h and decent thermal stability is realized in SM-s-Bu:BO-4Cl. This work highlights that the isomeric terminal alkyl with a branching point directly connected to the backbone for SMDs is a promising strategy for improving the crystal packing and film morphology and achieving highly efficient and stable ASM-OSCs.

Original language	English
Article number	2300878
Journal	Advanced Functional Materials
Volume	33
Issue number	25
DOIs	https://doi.org/10.1002/adfm.202300878
Publication status	Published - 2023 Jun 19

Bibliographical note

Funding Information:
This work was financially supported by grants from the Natural Science Foundation of China (No. 21971014 and 22275017). J.‐L.W. was supported by the Thousand Youth Talents Plan of China and BIT Teli Young Fellow Recruitment Program. H.‐F.Z. thanks Prof. Qiaoshi An for devices optimization. H.‐F.Z. thanks H.Z. for the synthesis and single‐crystal preparation of the model compounds. The authors also thank Prof. Xiong Li for the help on the TPV, TPC, and photo‐CELIV experiments. The authors also thank Prof. Yapei Wang and Bin Fu for the help on the contact angles experiments. The authors gratefully acknowledge the Analysis & Testing Center, Beijing Institute of Technology, for NMR, TGA, AFM, devices preparation, and characterization.

Funding Information:
This work was financially supported by grants from the Natural Science Foundation of China (No. 21971014 and 22275017). J.-L.W. was supported by the Thousand Youth Talents Plan of China and BIT Teli Young Fellow Recruitment Program. H.-F.Z. thanks Prof. Qiaoshi An for devices optimization. H.-F.Z. thanks H.Z. for the synthesis and single-crystal preparation of the model compounds. The authors also thank Prof. Xiong Li for the help on the TPV, TPC, and photo-CELIV experiments. The authors also thank Prof. Yapei Wang and Bin Fu for the help on the contact angles experiments. The authors gratefully acknowledge the Analysis & Testing Center, Beijing Institute of Technology, for NMR, TGA, AFM, devices preparation, and characterization.

Publisher Copyright:
© 2023 Wiley-VCH GmbH.

Keywords

organic solar cells
single crystals
small molecule donors
storage stability terminal alkyl chain engineering

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Condensed Matter Physics
Chemistry(all)
Materials Science(all)
Electrochemistry
Biomaterials

Access to Document

10.1002/adfm.202300878

Cite this

Zhi, H. F., Jiang, M., Zhang, H., An, Q., Bai, H. R., Jee, M. H., Woo, H. Y., Li, D., Huang, X., & Wang, J. L. (2023). Isomeric Small Molecule Donor with Terminal Branching Position Directly Attached to the Backbone Enables Efficient All-Small-Molecule Organic Solar Cells with Excellent Stability. Advanced Functional Materials, 33(25), Article 2300878. https://doi.org/10.1002/adfm.202300878

Isomeric Small Molecule Donor with Terminal Branching Position Directly Attached to the Backbone Enables Efficient All-Small-Molecule Organic Solar Cells with Excellent Stability. / Zhi, Hong Fu; Jiang, Mengyun; Zhang, Heng et al.
In: Advanced Functional Materials, Vol. 33, No. 25, 2300878, 19.06.2023.

Research output: Contribution to journal › Article › peer-review

Zhi, HF, Jiang, M, Zhang, H, An, Q, Bai, HR, Jee, MH, Woo, HY, Li, D, Huang, X & Wang, JL 2023, 'Isomeric Small Molecule Donor with Terminal Branching Position Directly Attached to the Backbone Enables Efficient All-Small-Molecule Organic Solar Cells with Excellent Stability', Advanced Functional Materials, vol. 33, no. 25, 2300878. https://doi.org/10.1002/adfm.202300878

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title = "Isomeric Small Molecule Donor with Terminal Branching Position Directly Attached to the Backbone Enables Efficient All-Small-Molecule Organic Solar Cells with Excellent Stability",

abstract = "All-small-molecule organic solar cells (ASM-OSCs) are challenging for their inadequate efficiency and device stability due to their more susceptive morphology. Herein, a family of isomeric small molecule donors (SMDs) is synthesized based on the benzodithiophene–terthiophene core with linear, 1st carbon, and 2nd carbon position branched butyl-based rhodanine for ASM-OSCs, respectively. The single crystal of thiophene-substituted model T-s-Bu forms a more compact intermolecular packing with herringbone structure than slip-layered packing-based T-n-Bu and T-i-Bu. SM-i-Bu and SM-s-Bu show slightly blue-shifted absorption and deepened HOMO levels in the neat film compared to SM-n-Bu. SM-s-Bu:BO-4Cl blend films have distinct face-on packing orientations and suitable fibrous phase separation along with more apparent microcrystals. Finally, SM-s-Bu:BO-4Cl-based device yields an improved power conversion efficiency of 16.06% compared to 15.12% and 8.22% for SM-n-Bu:BO-4Cl and SM-i-Bu:BO-4Cl, which is one of the top-ranked results for BTR-series SMDs in binary ASM-OSCs. More importantly, the excellent storage stability with a T80 lifetime of over 1700 h and decent thermal stability is realized in SM-s-Bu:BO-4Cl. This work highlights that the isomeric terminal alkyl with a branching point directly connected to the backbone for SMDs is a promising strategy for improving the crystal packing and film morphology and achieving highly efficient and stable ASM-OSCs.",

keywords = "organic solar cells, single crystals, small molecule donors, storage stability terminal alkyl chain engineering",

author = "Zhi, {Hong Fu} and Mengyun Jiang and Heng Zhang and Qiaoshi An and Bai, {Hai Rui} and Jee, {Min Hun} and Woo, {Han Young} and Danwei Li and Xuebin Huang and Wang, {Jin Liang}",

note = "Funding Information: This work was financially supported by grants from the Natural Science Foundation of China (No. 21971014 and 22275017). J.‐L.W. was supported by the Thousand Youth Talents Plan of China and BIT Teli Young Fellow Recruitment Program. H.‐F.Z. thanks Prof. Qiaoshi An for devices optimization. H.‐F.Z. thanks H.Z. for the synthesis and single‐crystal preparation of the model compounds. The authors also thank Prof. Xiong Li for the help on the TPV, TPC, and photo‐CELIV experiments. The authors also thank Prof. Yapei Wang and Bin Fu for the help on the contact angles experiments. The authors gratefully acknowledge the Analysis & Testing Center, Beijing Institute of Technology, for NMR, TGA, AFM, devices preparation, and characterization. Funding Information: This work was financially supported by grants from the Natural Science Foundation of China (No. 21971014 and 22275017). J.-L.W. was supported by the Thousand Youth Talents Plan of China and BIT Teli Young Fellow Recruitment Program. H.-F.Z. thanks Prof. Qiaoshi An for devices optimization. H.-F.Z. thanks H.Z. for the synthesis and single-crystal preparation of the model compounds. The authors also thank Prof. Xiong Li for the help on the TPV, TPC, and photo-CELIV experiments. The authors also thank Prof. Yapei Wang and Bin Fu for the help on the contact angles experiments. The authors gratefully acknowledge the Analysis & Testing Center, Beijing Institute of Technology, for NMR, TGA, AFM, devices preparation, and characterization. Publisher Copyright: {\textcopyright} 2023 Wiley-VCH GmbH.",

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N1 - Funding Information: This work was financially supported by grants from the Natural Science Foundation of China (No. 21971014 and 22275017). J.‐L.W. was supported by the Thousand Youth Talents Plan of China and BIT Teli Young Fellow Recruitment Program. H.‐F.Z. thanks Prof. Qiaoshi An for devices optimization. H.‐F.Z. thanks H.Z. for the synthesis and single‐crystal preparation of the model compounds. The authors also thank Prof. Xiong Li for the help on the TPV, TPC, and photo‐CELIV experiments. The authors also thank Prof. Yapei Wang and Bin Fu for the help on the contact angles experiments. The authors gratefully acknowledge the Analysis & Testing Center, Beijing Institute of Technology, for NMR, TGA, AFM, devices preparation, and characterization. Funding Information: This work was financially supported by grants from the Natural Science Foundation of China (No. 21971014 and 22275017). J.-L.W. was supported by the Thousand Youth Talents Plan of China and BIT Teli Young Fellow Recruitment Program. H.-F.Z. thanks Prof. Qiaoshi An for devices optimization. H.-F.Z. thanks H.Z. for the synthesis and single-crystal preparation of the model compounds. The authors also thank Prof. Xiong Li for the help on the TPV, TPC, and photo-CELIV experiments. The authors also thank Prof. Yapei Wang and Bin Fu for the help on the contact angles experiments. The authors gratefully acknowledge the Analysis & Testing Center, Beijing Institute of Technology, for NMR, TGA, AFM, devices preparation, and characterization. Publisher Copyright: © 2023 Wiley-VCH GmbH.

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Y1 - 2023/6/19

N2 - All-small-molecule organic solar cells (ASM-OSCs) are challenging for their inadequate efficiency and device stability due to their more susceptive morphology. Herein, a family of isomeric small molecule donors (SMDs) is synthesized based on the benzodithiophene–terthiophene core with linear, 1st carbon, and 2nd carbon position branched butyl-based rhodanine for ASM-OSCs, respectively. The single crystal of thiophene-substituted model T-s-Bu forms a more compact intermolecular packing with herringbone structure than slip-layered packing-based T-n-Bu and T-i-Bu. SM-i-Bu and SM-s-Bu show slightly blue-shifted absorption and deepened HOMO levels in the neat film compared to SM-n-Bu. SM-s-Bu:BO-4Cl blend films have distinct face-on packing orientations and suitable fibrous phase separation along with more apparent microcrystals. Finally, SM-s-Bu:BO-4Cl-based device yields an improved power conversion efficiency of 16.06% compared to 15.12% and 8.22% for SM-n-Bu:BO-4Cl and SM-i-Bu:BO-4Cl, which is one of the top-ranked results for BTR-series SMDs in binary ASM-OSCs. More importantly, the excellent storage stability with a T80 lifetime of over 1700 h and decent thermal stability is realized in SM-s-Bu:BO-4Cl. This work highlights that the isomeric terminal alkyl with a branching point directly connected to the backbone for SMDs is a promising strategy for improving the crystal packing and film morphology and achieving highly efficient and stable ASM-OSCs.

AB - All-small-molecule organic solar cells (ASM-OSCs) are challenging for their inadequate efficiency and device stability due to their more susceptive morphology. Herein, a family of isomeric small molecule donors (SMDs) is synthesized based on the benzodithiophene–terthiophene core with linear, 1st carbon, and 2nd carbon position branched butyl-based rhodanine for ASM-OSCs, respectively. The single crystal of thiophene-substituted model T-s-Bu forms a more compact intermolecular packing with herringbone structure than slip-layered packing-based T-n-Bu and T-i-Bu. SM-i-Bu and SM-s-Bu show slightly blue-shifted absorption and deepened HOMO levels in the neat film compared to SM-n-Bu. SM-s-Bu:BO-4Cl blend films have distinct face-on packing orientations and suitable fibrous phase separation along with more apparent microcrystals. Finally, SM-s-Bu:BO-4Cl-based device yields an improved power conversion efficiency of 16.06% compared to 15.12% and 8.22% for SM-n-Bu:BO-4Cl and SM-i-Bu:BO-4Cl, which is one of the top-ranked results for BTR-series SMDs in binary ASM-OSCs. More importantly, the excellent storage stability with a T80 lifetime of over 1700 h and decent thermal stability is realized in SM-s-Bu:BO-4Cl. This work highlights that the isomeric terminal alkyl with a branching point directly connected to the backbone for SMDs is a promising strategy for improving the crystal packing and film morphology and achieving highly efficient and stable ASM-OSCs.

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Isomeric Small Molecule Donor with Terminal Branching Position Directly Attached to the Backbone Enables Efficient All-Small-Molecule Organic Solar Cells with Excellent Stability

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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