journal article·2021-03

1,2,4-Triazoline-3,5-dione substituted perylene diimides as near infrared acceptors for bulk heterojunction organic solar cells

Xia Liu, Ming Hu, Yongle Li, Xiaohong Zhao, Youdi Zhang, Yu Hu, Zhongyi Yuan, Yiwang Chen

Dyes and Pigments· Volume 187
Publisher page

Abstract

Abstract A series of perylene diimide derivatives (PDIs) with near infrared (NIR) absorption and different geometries were synthesized by introducing 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) and 4-butyl-1,2,4-triazoline-3,5-dione (BuTAD) to the bay position of PDIs through the Diels–Alder reaction. The compounds with various twisted three-dimensional (3D) structures were obtained through combining different connection units, and their aggregation and domain size of the donor-acceptor blends were adjusted. All of these compounds exhibit broad absorption in the range of 300–860 nm, high thermal stability (with a decomposition temperature over 350 °C), applicable lowest unoccupied molecular orbital energy levels (−3.70 ~ −3.74 eV), and appropriate solubility. Blending with a PM6 polymer donor, bulk heterojunction organic solar cells (BHJ OSCs) based on BDT-SBuTADPDI2 exhibited the highest power conversion efficiency of 2.74%. Their carrier mobility and morphology were investigated by Space-charge-limited current (SCLC) measurements and Atomic Force Microscopy (AFM) measurements respectively. This study provides a promising strategy to construct potential PDI-based acceptors with NIR absorption.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Organic Electronics and Photovoltaics · Conducting polymers and applications · Perovskite Materials and Applications

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (49)

Show source-provided references
1. High-performance organic bulk-heterojunction solar cells based on multiple-donor or multiple-acceptor components10.1002/adma.201705706 ↗
2. Progress in the synthesis of perylene bisimide dyes10.1039/C8QO01368C ↗
3. “Double-acceptor-type” random conjugated terpolymer donors for additive-free non-fullerene organic solar cells10.1021/acsami.0c02862 ↗
4. High-efficiency nonfullerene organic solar cells enabled by 1000 nm thick active layers with a low trap-state density10.1021/acsami.0c05172 ↗
5. Synthesis and property study of phthalocyanine tetraimides as solution processable electron acceptors10.1016/j.dyepig.2019.107980 ↗
6. Wide band-gap two-dimension conjugated polymer donors with different amounts of chlorine substitution on alkoxyphenyl conjugated side chains for non-fullerene polymer solar cells10.1007/s10118-020-2435-5 ↗
7. Seleno twisted benzodiperylenediimides: facile synthesis and excellent electron acceptors for additive-free organic solar cells10.1039/C8CC09367A ↗
8. A terminally tetrafluorinated nonfullerene acceptor for well‐performing alloy ternary solar cells10.1002/adfm.201805872 ↗
9. Single-junction organic solar cell with over 15% efficiency using fused-ring acceptor with electron-deficient core10.1016/j.joule.2019.01.004 ↗
10. Non-fullerene small molecule acceptors based on perylene diimides10.1039/C6TA06978A ↗
11. Optimized active layer morphologies via ternary copolymerization of polymer donors for 17.6% efficiency organic solar cells with enhanced fill factor
12. Achieving efficient inverted perovskite solar cells with excellent electron transport and stability by employing a ladder-conjugated perylene diimide dimer10.1039/C9TA09260A ↗
13. A simple molecular structure of ortho-derived perylene diimide diploid for non-fullerene organic solar cells with efficiency over 8%10.1039/C7TA06804B ↗
14. Soluble ladder conjugated polymer composed of perylenediimides and thieno[3,2-b]thiophene (LCPT): a highly efficient synthesis via photocyclization with the sunlight10.1021/ma1026252 ↗
15. Recent development of perylene diimide-based small molecular non-fullerene acceptors in organic solar cells10.1016/j.cclet.2017.08.025 ↗
16. Heterologous perylene diimide arrays: potential non-fullerene acceptors in organic solar cells10.1039/C7TC03171H ↗
17. Controllable monobromination of perylene ring system: synthesis of bay-functionalized perylene dyes10.1021/acs.joc.7b02540 ↗
18. Rationalizing device performance of perylenediimide derivatives as acceptors for bulk-heterojunction organic solar cells10.1016/j.orgel.2018.11.006 ↗
19. Ring-fusion of perylene diimide acceptor enabling efficient nonfullerene organic solar cells with a small voltage loss10.1021/jacs.7b09998 ↗
20. Near-infrared electron acceptors with fluorinated regioisomeric backbone for highly efficient polymer solar cells10.1002/adma.201803769 ↗
21. Molecular helices as electron acceptors in high-performance bulk heterojunction solar cells10.1038/ncomms9242 ↗
22. N-annulated perylene diimide dimers: the effect of thiophene bridges on physical, electronic, optical, and photovoltaic properties10.1039/C7SE00056A ↗
23. A tetraperylene diimides based 3D nonfullerene acceptor for efficient organic photovoltaics10.1002/advs.201500014 ↗
24. Rylene and rylene diimides: comparison of theoretical and experimental results and prediction for high-rylene derivatives10.1021/acs.jpca.6b07552 ↗
25. A C2-symmetric triple [5]helicene based on N-annulated triperylene hexaimide for chiroptical electronics10.1007/s11426-019-9632-2 ↗
26. Near-infrared electron acceptors based on terrylene diimides for organic solar cells10.1039/C8TA08186G ↗
27. Nonfullerene-acceptor all-small-molecule organic solar cells based on highly twisted perylene bisimide with an efficiency of over 610.1021/acsami.6b13721 ↗
28. Interfacial ZnO modification using a carboxylic acid functionalized N-annulated perylene diimide for inverted type organic photovoltaics10.1021/acsaelm.9b00328 ↗
29. Palladium-catalyzed Si-C bond formation toward sila-annulated perylene diimides10.1021/acs.orglett.7b02011 ↗
30. Core-fluorinated naphthalene diimides: synthesis, characterization, and application in n-type organic field-effect transistors10.1021/acs.orglett.5b03489 ↗
31. An approach to novel NIR dyes utilising α-effect donor groups10.1016/S0143-7208(03)00083-4 ↗
32. Constructing a donor–acceptor linear-conjugation structure for heterologous perylene diimides to greatly improve the photovoltaic performance10.1039/C8TC04929G ↗
33. Perylene diimide trimers based bulk heterojunction organic solar cells with efficiency over 7%10.1002/aenm.201600060 ↗
34. Nonfullerene acceptors with an N-annulated perylene core and two perylene diimide units for efficient organic solar cells10.1016/j.dyepig.2019.107970 ↗
35. Rigidifying nonplanar perylene diimides by ring fusion toward geometry-tunable acceptors for high-performance fullerene-free solar cells10.1002/adma.201504120 ↗
36. Methane-perylene diimide-based small molecule acceptors for high efficiency non-fullerene organic solar cells10.1039/C9TC03457A ↗
37. A perylene diimide electron acceptor with a triphenylamine core: promoting photovoltaic performance via hot spin-coating
38. A simple perylene diimide derivative with a highly twisted geometry as an electron acceptor for efficient organic solar cells10.1039/C6TA04232E ↗
39. Fusion or non-fusion of quasi-two-dimensional fused perylene diimide acceptors: the importance of molecular geometry for fullerene-free organic solar cells10.1039/C9TA10174H ↗
40. Singlet relaxation dynamics and long triplet lifetimes of thiophene-coupled perylene diimides dyads: new insights for high efficiency organic solar cells10.1016/j.cclet.2020.06.018 ↗
41. A 9,9'-spirobi[9H-fluorene]-cored perylenediimide derivative and its application in organic solar cells as a non-fullerene acceptor10.1039/C5CC08484A ↗
42. Efficient combination of ionic liquids and microwave irradiation as a green protocol for polycondensation of 4-(3-hydroxynaphthalene)-1,2,4-triazolidine-3,5-dione with diisocyanates10.1016/j.polymer.2007.07.036 ↗
43. Tandem functionalization in a highly branched polymer with layered structure10.1002/chem.201800683 ↗
44. Synthesis and anti-leishmanial activity of heterocyclic betulin derivatives10.1016/j.bmc.2010.01.003 ↗
45. Effect of substituents of twisted benzodiperylenediimides on non-fullerene solar cells10.1016/j.orgel.2017.04.032 ↗
46. Sulfur-substituted perylene diimides: efficient tuning of LUMO levels and visible-light absorption via sulfur redox10.1039/C9CC07040K ↗
47. Electronic structures of molecules X. Aldehydes, ketones and related molecules10.1063/1.1749730 ↗
48. Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures10.1039/B401630K ↗
49. Non-fullerene acceptors for organic photovoltaics: an emerging horizon10.1039/C4MH00042K ↗