Synthesis and Properties of Novel A-D-A Type Molecules with Non-Fused Azacyclic End Groups

doi:10.6023/cjoc202409031

Chinese Journal of Organic Chemistry Previous Articles

ARTICLE

一种具有非稠合氮杂环端基的A-D-A型分子的合成及性能研究

刘文睿^a, 音正春^b, 叶世棋^a, 徐智伟^a, 陈龙^a, 王官武^a,b,c,*

^a中国科学技术大学化学系安徽合肥 230026;
^b功能分子固体教育部重点实验室、分子基材料安徽省重点实验室、安徽师范大学化学与材料科学学院安徽芜湖 241002;
^c兰州大学应用有机化学国家重点实验室甘肃兰州 730000

收稿日期:2024-09-23 修回日期:2024-10-23
基金资助:
国家自然科学基金(No. 22271271)资助项目.

Synthesis and Properties of Novel A-D-A Type Molecules with Non-Fused Azacyclic End Groups

Wen-Rui Liu^a, Zheng-Chun Yin^b, Shi-Qi Ye^a, Zhiwei Xu^a, Long Chen^a, Guan-Wu Wang^a,b,c,*

^aDepartment of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026;
^bKey Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials, and School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241002;
^cState Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000

Received:2024-09-23 Revised:2024-10-23
Contact: * E-mail: gwang@ustc.edu.cn.
Supported by:
National Natural Science Foundation of China (No. 22271271) .

1. .pdf(2823KB)

Abstract

Acceptor-donor-acceptor (A-D-A) type molecules, of which the novel non-fused azacyclic end-group pyrazolinones were modified with chlorine substitution on the phenyl ring, were synthesized. The non-fused azacyclic end-group pyrazolinones have the advantages of simple synthesis steps, low cost and environmental friendliness, compared to the classical end-group dicyanomethyleneindianone. The properties of the synthesized A-D-A type molecules with non-fused azacyclic end groups were characterized by theoretical calculation, UV-vis absorption, cyclic voltammetry, X-ray diffraction and space charge limited current. It was shown that the strong UV-vis absorptions of the synthesized A-D-A type molecules were located in the wavelength range of 500-700 nm, with a moderate band gap of nearly 1.7 eV. At the same time, the influence of end-group chlorination on the properties of A-D-A type molecules was compared and explored. It was proven that this kind of A-D-A type molecules with non-fused azacyclic end groups have the potential to be applied as interfacial modified layer of the active layer in perovskite solar cell devices.

Key words: A-D-A type molecule, N-type semiconductor, Non-fused end groups, Medium bandgap

Cite this article

Wen-Rui Liu, Zheng-Chun Yin, Shi-Qi Ye, Zhiwei Xu, Long Chen, Guan-Wu Wang. Synthesis and Properties of Novel A-D-A Type Molecules with Non-Fused Azacyclic End Groups[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202409031.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Yu G.; Gao J.; Hummelen J. C.; Wudl F.; Heeger A. J. Science 1995, 270, 1789-1791.
[2] Dou L.; Liu Y.; Hong Z.; Li G.; Yang Y. Chem.Rev. 2015, 115, 12633-12665.
[3] Yao H.; Ye L.; Zhang H.; Li S.; Zhang S.; Hou J. Chem.Rev. 2016, 116, 7397-7457.
[4] Meng L.; Zhang Y.; Wan X.; Li C.; Zhang X.; Wang Y.; Ke X.; Xiao Z.; Ding L.; Xia R.; Yip H.-L.; Cao Y.; Chen Y. Science 2018, 361, 1094-1098.
[5] Cui Y.; Xu Y.; Yao H.; Bi P.; Hong L.; Zhang J.; Zu Y.; Zhang T.; Qin J.; Ren J.; Chen Z.; He C.; Hao X.; Wei Z.; Hou J. Adv.Mater. 2021, 33, e2102420.
[6] Chong K.; Xu X.; Meng H.; Xue J.; Yu L.; Ma W.; Peng Q. Adv.Mater. 2022, 34, e2109516.
[7] He C.; Pan Y.; Ouyang Y.; Shen Q.; Gao Y.; Yan K.; Fang J.; Chen Y.; Ma C.-Q.; Min J.; Zhang C.; Zuo L.; Chen H.Energy Environ. Sci. 2022, 15, 2537-2544.
[8] Zhang G.; Lin F. R.; Qi F.; Heumüller T.; Distler A.; Egelhaaf H.-J.; Li N.; Chow P. C.Y.; Brabec, C. J.; Jen, A. K.-Y.; Yip, H.-L. Chem. Rev. 2022, 122, 14180-14274.
[9] Lin Y.; Wang J.; Zhang Z. G.; Bai H.; Li Y.; Zhu D.; Zhan X. Adv.Mater. 2015, 27, 1170-1174.
[10] Lin Y.; Zhao F.; Prasad S. K.K.; Chen, J. D.; Cai, W.; Zhang, Q.; Chen, K.; Wu, Y.; Ma, W.; Gao, F.; Tang, J. X.; Wang, C.; You, W.; Hodgkiss, J. M.; Zhan, X. Adv. Mater. 2018, 30, e1706363.
[11] Yuan J.; Zhang Y.; Zhou L.; Zhang G.; Yip H.-L.; Lau T.-K.; Lu X.; Zhu C.; Peng H.; Johnson P. A.; Leclerc M.; Cao Y.; Ulanski J.; Li Y.; Zou Y. Joule 2019, 3, 1140-1151.
[12] Cheng P.; Li G.; Zhan X.; Yang Y. Nat. Photonics 2018, 12, 131-142.
[13] Li M.; Zhou Y.; Zhang J.; Song J.; Bo Z. J. Mater. Chem. A 2019, 7, 8889-8896.
[14] Yan C.; Barlow S.; Wang Z.; Yan H.; Jen A. K.Y.; Marder, S. R.; Zhan, X. Nat. Rev. Mater. 2018, 3, 18003.
[15] Zhu L.; Zhang M.; Xu J.; Li C.; Yan J.; Zhou G.; Zhong W.; Hao T.; Song J.; Xue X.; Zhou Z.; Zeng R.; Zhu H.; Chen C.-C.; MacKenzie, R. C. I.; Zou, Y.; Nelson, J.; Zhang, Y.; Sun, Y.; Liu, F. Nat. Mater. 2022, 21, 656-663.
[16] Zhang C.; Song J.; Ye L.; Li X.; Jee M. H.; Woo H. Y.; Sun Y. Angew. Chem. Int. Ed. 2024, 63, e202316295.
[17] Li X.; Luo S.; Sun H.; Sung H. H.-Y.; Yu, H.; Liu, T.; Xiao, Y.; Bai, F.; Pan, M.; Lu, X.; Williams, I. D.; Guo, X.; Li, Y.; Yan, H. Energy Environ. Sci. 2021, 14, 4555.
[18] Jiang K.; Wei Q.; Lai J. Y.L.; Peng, Z.; Kim, H. K.; Yuan, J.; Ye, L.; Ade, H.; Zou, Y.; Yan, H. Joule 2019, 3, 3020-3033.
[19] Li C.; Zhou J.; Song J.; Xu J.; Zhang H.; Zhang X.; Guo J.; Zhu L.; Wei D.; Han G.; Min J.; Zhang Y.; Xie Z.; Yi Y.; Yan H.; Gao F.; Liu F.; Sun Y. Nat. Energy 2021, 6, 605.
[20] Qiao Y.; Liu X.; Li Y.; Guo X.; Li C. J. Mater. Chem. A 2024, 12, 5493-5498.
[21] Chen Z.; Zhang S.; Zhang T.; Ren J.; Dai J.; Li H.; Qiao J.; Hao X.; Hou J. Angew. Chem. Int. Ed. 2024, 63, e202317892.
[22] Luo D.; Zhang L.; Zeng J.; Chi W.; Zhou J.; Zhou E.; Li L.; Iwahashi T.; Michinobu T.; Ouchi Y.; Xu B.; Kyaw A. K.K. Adv. Funct. Mater. 2024, 34, 2311736.
[23] Gao Y.; Yang X.; Sun R.; Xu L.-Y.; Chen Z.; Zhang M.; Zhu H.; Min J. Joule 2023, 7, 2845-2858.
[24] Shi S.; Zhang S.; Yao X.; Xian K.; Han D.; Zhu Y.; Li Y.; Tu X.; Tang Z.; Ye L.; Zhong H.; Fei Z. J. Mater. Chem. C 2023, 11, 11943.
[25] Yang Q.; Liu X.; Yu S.; Feng Z.; Liang L.; Qin W.; Wang Y.; Hu X.; Chen S.; Feng Z.; Hou G.; Wu K.; Guo X.; Li C.Energy Environ. Sci. 2021, 14, 6536
[26] Shi Y.; Zhu L.; Yan Y.; Xie M.; Liang G.; Qiao J.; Zhang J.; Hao X.; Lu, Kun; Wei, Z. Adv.Energy Mater. 2023, 13, 2300458.
[27] Yu H.; Wang Y.; Zou X.; Han H.; Kim H. K.; Yao Z.; Wang Z.; Li Y.; Ng H. M.; Zhou W.; Zhang J.; Chen S.; Lu X.; Wong K. S.; Zhu Z.; Yan H.; Hu H. Adv. Funct. Mater. 2023, 33, 2300712.
[28] Li H.; Li J.; Yang C.; Wang J.; Ryu D. H.; Ma L.; Yang Y.; Shin W. S.; Zhang S.; Hou J. J. Mater. Chem. C 2023, 11, 6155.
[29] Luo Z.; Yan H.; Yang C. Acc. Mater. Res. 2023, 4, 968-981.
[30] Pan M.-A.; Lau T.-K.; Tang Y.; Wu Y.-C.; Liu T.; Li K.; Chen M.-C.; Lu X.; Ma W.; Zhan C. J. Mater. Chem. A 2019, 7, 20713-20722.
[31] An Q.; Ma X.; Gao J.; Zhang F. Sci.Bull. 2019, 64, 504-506.
[32] Li K.; Wu Y.; Tang Y.; Pan M.-A.; Ma W.; Fu H.; Zhan C.; Yao J. Adv.Energy Mater. 2019, 9, 1901728.
[33] Jiang B.-H.; Chen C.-P.; Liang H.-T.; Jeng R.-J.; Chien W.-C.; Yu Y.-Y.Dyes Pigm. 2020, 181, 108613.
[34] Elsayed M. H.; Jiang B.-H.; Wang Y.-P.; Chang P.-Y.; Chiu Y.-C.; Jeng R.-J.; Chou H.-H.; Chen C.-P.J. Mater. Chem. A 2021, 9, 9780-9790.
[35] Fan B.; Gao W.; Wang Y.; Zhong W.; Lin F.; Li W. J.; Huang F.; Yu K.-M.; Jen A. K.Y. ACS Energy Lett. 2021, 6, 3522-3529.
[36] Li Y.; Guo Y.; Chen Z.; Zhan L.; He C.; Bi Z.; Yao N.; Li S.; Zhou G.; Yi Y.; Yang Y.; Zhu H.; Ma W.; Gao F.; Zhang F.; Zuo L.; Chen H.Energy Environ. Sci. 2022, 15, 855-865.
[37] Ma R.; Yan C.; Yu J.; Liu T.; Liu H.; Li Y.; Chen J.; Luo Z.; Tang B.; Lu X.; Li G.; Yan H. ACS Energy Lett. 2022, 7, 2547-2556.
[38] Murugan P.; Hu T.; Hu X.; Chen Y. J. Mater. Chem. A 2022, 10, 17968-17987.
[39] Song K. C.; Kim B. J.; Sung W.; Han S. G.; Chung S.; Lee J.; Cho K. J. Mater. Chem. C 2023, 11, 5354-5362.
[40] Trippodo E.; Campisciano V.; Feng L.-W.; Chen Y.; Huang W.; Alzola J. M.; Zheng D.; Sangwan V. K.; Hersam M. C.; Wasielewski M. R.; Pignataro B.; Giacalone F.; Marks T. J.; Facchetti A. J. Mater. Chem. C 2023, 11, 8074-8083.
[41] Han C.; Wang J.; Zhang S.; Chen L.; Bi F.; Wang J.; Yang C.; Wang P.; Li Y.; Bao X. Adv.Mater. 2023, 35, 2208986.
[42] Kim K. S.; Chung Y.; Praba L.; Kim D.; Park J. B.; Jung J. W. Org. Electron. 2024, 125, 106976.
[43] Pu Z.; Li J.; Xie L.; Tong X.; Yang S.; Liu J.; Chen J.; Yang M.; Yang D.; Ge Z. Small 2024, 20, 2310742.
[44] Liu Z.; Lee E. C.Sustain. Energy Fuels 2021, 5, 2354-2361.
[45] Yang G.; Afraj S. N.; Li J.; Zhang D.; Fan P.; Chen M. C.; Zheng D.; Yu J. J. Mater. Chem. C 2024, 12, 3482-3489.
[46] Song C.; Li X.; Wang Y.; Fu S.; Wan L.; Liu S.; Zhang W.; Song W.; Fang J. J. Mater. Chem. A 2019, 7, 19881-19888.
[47] Kuklin S. A.; Safronov S. V.; Fedorovskii O. Y.; Khakina E. A.; Peregudov A. S.; Ezernitskaya M. G.; Komissarova E. A.; Emelianov N. A.; Uvarov M. N.; Kulik L. V.; Frolova L. A.; Troshin P. A.; Khokhlov A. R. Org. Electron. 2024, 125, 106978.
[48] Min J.; Luponosov Y. N.; Cui C.; Kan B.; Chen H.; Wan X.; Chen Y.; Ponomarenko S. A.; Li Y.; Brabec C. J. Adv. Energy Mater. 2017, 7, 1700465.
[49] Zhang G.; Zhao J.; Chow P. C.Y.; Jiang, K.; Zhang, J.; Zhu, Z.; Zhang, J.; Huang, F.; Yan, H. Chem. Rev. 2018, 118, 3447-3507.
[50] Li X.; Pan F.; Sun C.; Zhang M.; Wang Z.; Du J.; Wang J.; Xiao M.; Xue L.; Zhang Z. G.; Zhang C.; Liu F.; Li Y. Nat.Commun. 2019, 10, 519.
[51] Pu Z.; Li J.; Xie L.; Tong X.; Yang S.; Liu J.; Chen J.; Yang M.; Yang D.; Ge Z. Small 2024, 20, 2310742.
[52] Wang H.; Zhang C.; Yao Y.; Cheng C.; Wang K. Small 2024, 2403193.
[53] Yang G.; Afraj S. N.; Li J.; Zhang D.; Fan P.; Chen M.-C.; Zheng D.; Yu J. J. Mater. Chem. C 2024, 12, 3482.
[54] Yang W.; Wang W.; Wang Y.; Sun R.; Guo J.; Li H.; Shi M.; Guo J.; Wu Y.; Wang T.; Lu G.; Brabec C. J.; Li Y.; Min J. Joule 2021, 5, 1209-1230.
[55] Min J.; Luponosov Y. N.; Cui C.; Kan B.; Chen H.; Wan X.; Chen Y.; Ponomarenko S. A.; Li Y.; Brabec C. J. Adv. Energy Mater. 2017, 7, 1700465.
[56] Cui Y.; Yao H.; Zhang J.; Xian K.; Zhang T.; Hong L.; Wang Y.; Xu Y.; Ma K.; An C.; He C.; Wei Z.; Gao F.; Hou J. Adv.Mater. 2020, 32, 1908205.
[57] Lin F.; Jiang K.; Kaminsky W.; Zhu Z.; Jen A. K.-Y. J. Am. Chem. Soc. 2020, 142, 15246-15251.
[58] Yang G.; Afraj S. N.; Li J.; Zhang D.; Fan P.; Chen M.-C.; Zheng D.; Yu J. J. Mater. Chem. C 2024, 12, 3482-3489.
[59] Yang Q.; Liu X.; Yu S.; Feng Z.; Liang L.; Qin W.; Wang Y.; Hu X.; Chen S.; Feng Z.; Hou G.; Wu K.; Guo X.; Li C.Energy Environ. Sci. 2021, 14, 6536-6545.
[60] Afraj S. N.; Velusamy A.; Chen C.-Y.; Ni J.-S.; Ezhumalai Y.; Pan C.-H.; Chen K.-Y.; Yau S.-L.; Liu C.-L.; Chiang C.-H.; Wu C.-G.; Chen M.-C.J. Mater. Chem. A 2022, 10, 11254-11267.
[61] Wang D.; Ye T.; Zhang Y. J. Mater. Chem. A 2020, 8, 20819-20848.
[62] Tavakoli M. M.; Yadav P.; Prochowicz D.; Sponseller M.; Osherov A.; Bulovic´ V.; Kong J. Adv.Energy Mater. 2019, 9, 201803587
[63] Zhou T.; Wang K.; Zhu, D. ; Kuang, A. J. Phys. Chem. Lett. 2022, 13, 6074-6078
[64] Zhu Y.-F.; Wei B.-L.; Wei J.-J.; Wang W.-Q.; Song W.-B.; Xuan L.-J.Tetrahedron Lett. 2019, 60, 1202-1205.

一种具有非稠合氮杂环端基的A-D-A型分子的合成及性能研究

Synthesis and Properties of Novel A-D-A Type Molecules with Non-Fused Azacyclic End Groups

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 0

Recommended Articles

Metrics

Comments