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2023 , Vol. 43 >Issue 8: 2934 - 2945

DOI: https://doi.org/10.6023/cjoc202302019

研究论文

金属-有机框架衍生的植酸铁催化氢转移高效制备2-芳基苯并噁唑

  • 欧世国 ,
  • 柴瑞瑞 ,
  • 李家豪 ,
  • 王大伟 ,
  • 桑欣欣
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  • 江南大学化学与材料工程学院 教育部合成与生物胶体重点实验室 江苏无锡 214122

收稿日期: 2023-02-16

  修回日期: 2023-03-19

  网络出版日期: 2023-04-10

基金资助

国家自然科学基金(21803025)

收起

Metal-Organic Framework Derived Phytate-Iron for Efficient Synthesis of 2-Arylbenzoxazole via Hydrogen Transfer Strategy

  • Shiguo Ou ,
  • Ruirui Chai ,
  • Jiahao Li ,
  • Dawei Wang ,
  • Xinxin Sang
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  • Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu 214122
*E-mail: ;

Received date: 2023-02-16

  Revised date: 2023-03-19

  Online published: 2023-04-10

Supported by

The National Natural Science Foundation of China(21803025)

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摘要

金属有机框架及其衍生物在催化领域显示出巨大的应用潜力. 利用表面工程方法制备了ZIF-L-Co@phytate-iron (ZIF-L-Co@PA-Fe)异质金属-有机框架(MOF)衍生物. 首先, 通过植酸(PA)与ZIF-L-Co框架中的有机配体交换, 制备植酸功能化的ZIF-L-Co@PA材料. 然后, 通过Fe3＋与配体的配位合成了具有独特异质结构的ZIF-L-Co@PA-Fe. 得益于金属-配体相互作用的改进, 所设计的ZIF-L-Co@PA-Fe杂化物对氢转移反应表现出优异的催化活性. 以ZIF-L-Co@PA-Fe为催化剂, 在无溶剂条件下成功地实现了邻硝基苯酚与醇的转移氢环化反应, 得到2-取代苯并噁唑衍生物. 该催化反应不需要氧化剂、还原剂或碱等额外的添加剂. 此外, ZIF-L-Co@PA-Fe配合物具有良好的催化循环稳定性, 可重复使用5次而催化活性无明显下降. 本工作可为优化其他系列MOF衍生物的催化性能提供有效的指导.

关键词： 金属-有机框架; 离子交换; 多相催化; 氢转移

本文引用格式

欧世国 , 柴瑞瑞 , 李家豪 , 王大伟 , 桑欣欣 . 金属-有机框架衍生的植酸铁催化氢转移高效制备2-芳基苯并噁唑[J]. 有机化学, 2023 , 43(8) : 2934 -2945 . DOI: 10.6023/cjoc202302019

Abstract

Recently, metal-organic framework (MOF) and its derivatives showed great application potential in catalysis. ZIF-L-Co@phytate-iron (ZIF-L-Co@PA-Fe) heterogeneous MOF derivatives were synthesized by a facile surface engineering method. Phytic acid functionalized ZIF-L-Co (ZIF-L-Co@PA) was firstly prepared through organic ligand exchange of phytic acid (PA). Then, ZIF-L-Co@PA-Fe with unique heterostructure was prepared via coordination occurred between Fe3＋ and ligands. Benefiting from the greatly modify metal-ligand interactions, the as-designed ZIF-L-Co@PA-Fe hybrids exhibited excellent catalytic activities toward the hydrogen transfer reactions. 2-Substituted benzoxazole derivatives were successfully synthesized via transfer hydrogenative annulation of o-nitrophenol with alcohols catalyzed by ZIF-L-Co@PA-Fe under solvent-free conditions. No additional additives, such as oxidants, reductants or bases were required for this reaction. Moreover, ZIF-L-Co@PA-Fe coordination complex showed excellent reusability and could be recycled up to five times without obvious decline in its catalytic activity. This work may provide effective guidance for optimizing the catalytic performance of other series of MOF derivatives.

Key words： metal-organic framework; ion exchange; heterogeneous catalysis; hydrogen transfer

参考文献

[1]
(a) Demmer, C. S.; Bunch, L. Eur. J. Med. Chem. 2015, 97, 778.
[1]
(b) Jiang, B.; Shi, S. Chin. J. Org. Chem. 2022, 42, 3263. (in Chinese)
[1]
( 蒋滨阳, 施世良, 有机化学, 2022, 42, 3263.)
[1]
(c) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893.
[1]
(d) Li, J.; Liu, H.; Zhang, B.; Ge, B.; Wang, D. Chin. J. Org. Chem. 2022, 42, 619. (in Chinese)
[1]
( 李家豪, 刘洪强, 张博, 葛冰洋, 王大伟, 有机化学, 2022, 42, 619.)
[1]
(e) Asensio, J. A.; Sánchez, E. M.; Gomez-Romero, P. Chem. Soc. Rev. 2010, 39, 3210.
[1]
(f) Zhao, J.; Jin, Z.; Wang, R.; Zhang, X.; Han, Y.; Hu, C.; Liu, X.; Zhang, C.; Jin, L. Chin. J. Org. Chem. 2022, 42, 2172. (in Chinese)
[1]
( 赵静, 金辄, 王润, 张新庚, 韩英妹, 胡春, 刘晓平, 张传明, 金丽萍, 有机化学, 2022, 42, 2172.)
[1]
(g) Shi, Y. M.; Crames, J. J.; Czech, L.; Bozhüyük, K. A. J.; Shi, Y. N.; Hirschmann, M.; Lamberth, S.; Claus, P.; Paczia, N.; Rückert, C.; Kalinowski, J.; Bange, G.; Bode, H. B. Angew. Chem., Int. Ed. 2022, 134, e202206106.
[1]
(h) Tan, Z.; Jiang, H.; Zhang, M. Chem. Commun. 2016, 52, 9359.
[1]
(i) Yadav, G.; Ganguly, S. Eur. J. Med. Chem. 2015, 97, 419.
[1]
(j) Hikawa, H.; Ichinose, R.; Kikkawa, S.; Azumaya, I. Green Chem. 2018, 20, 1297.
[2]
(a) Saranya, T. V.; Sruthi, P. R.; Raj, V.; Anas, S. J. Organomet. Chem. 2021, 937, 121733.
[2]
(b) Mishra, N.; Singh, A. S.; Agrahari, A. K.; Singh, S. K.; Singh, M.; Tiwari, V. K. ACS Comb. Sci. 2019, 21, 389.
[2]
(c) Urzúa, J. I.; Contreras, R.; Salas, C. O.; Tapia, R. A. RSC Adv. 2016, 6, 82401.
[2]
(d) Zhao, M.; Yang, Z.; Yang, D. Chin. J. Org. Chem. 2022, 42, 111. (in Chinese)
[2]
( 赵咪娜, 杨梓墨, 杨得锁, 有机化学, 2022, 42, 111.)
[2]
(e) Hajipour, A. R.; Khorsandi, Z. A. New J. Chem. 2016, 40, 10474.
[2]
(f) Hao, S.; Yang, J.; Liu, P.; Xu, J., Yang, C.; Li, F. Org. Lett. 2021, 23, 2553.
[2]
(g) Hu, X.; Yang, B.; Yao, W.; Wang, D. Chin. J. Org. Chem. 2018, 38, 3296. (in Chinese)
[2]
( 胡昕宇, 杨伯斌, 姚玮, 王大伟, 有机化学, 2018, 38, 3296.)
[2]
(h) Saha, P.; Ramana, T.; Purkait, N.; Ashif, M. A.; Pau, R.; Punniyamurth, T. J. Org. Chem. 2009, 74, 8719.
[2]
(i) Tang, Y.; Li, M.; Gao, H.; Rao, G.; Mao, Z. RSC Adv. 2020, 10, 14317.
[3]
(a) Moghaddam, F. M.; Saberi, V.; Kalhor, S.; Veisi, N. Appl. Organomet. Chem. 2018, 32, e4240.
[3]
(b) Sahu, P. K. RSC Adv. 2017, 7, 42000.
[3]
(c) Li, Z.; Wang, Q.; Pu, M.; Yang, Z.; Lei, M. Acta Chim. Sinica 2020, 78, 437. (in Chinese)
[3]
( 李哲伟, 王骞阅, 蒲敏, 杨作银, 雷鸣, 化学学报, 2020, 78, 437.)
[3]
(d) Bahrami, K.; Bakhtiarian, M. ChemistrySelect 2018, 3, 10875.
[3]
(e) Liu, P.; Tung, N. T.; Xu, X.; Yang, J.; Feng, L. J. Org. Chem. 2021, 86, 2621.
[3]
(f) Shebitha, A. M.; Shaibuna, M.; Hiba, K.; Sreekuma, K. Catal. Lett. 2022, 152, 3017.
[3]
(g) Inamdar, S. M.; More, V. K.; Mandal, S. K. Tetrahedron Lett. 2013, 54, 579.
[3]
(h) Hikawa, H.; Nakayama, T.; Takahashi, M.; Kikkawa, S.; Azumaya, I. Adv. Synth. Catal. 2021, 363, 4075.
[3]
(i) Ma, C.; Huang, Y.; Zhao, Y. ACS Catal. 2016, 6, 6408.
[4]
(a) Ferlin, F.; van der Hulst, M. K.; Santoro, S.; Lanari, D.; Vaccaro, L. Green Chem. 2019, 21, 5298.
[4]
(b) Chen, R.; Jalili, Z.; Tayebee, R. RSC Adv. 2021, 11, 16359.
[4]
(c) Safaei, E.; Alaji, Z.; Panahi, F.; Wojtczak, A.; Jagli?i?, J. Z. New J. Chem. 2018, 42, 7230.
[4]
(d) Hu, J.; Li, M.; Wan, J.; Sun, J.; Gao, H.; Zhang, F.; Zhang, Z. Org. Biomol. Chem. 2022, 20, 3413.
[4]
(e) Khalafi-Nezhad, A.; Panahi, F. ACS Catal. 2014, 4, 1686.
[4]
(f) Jiang, H.; Zang, C.; Cheng, H.; Sun, B.; Gao, X. Catal. Sci. Technol. 2021, 11, 7955.
[4]
(g) Doan, S. H.; Tran, C. B.; Cao, An, L. N.; Le, N. T. H.; Phan, N. T. S. Catal. Lett. 2019, 149, 2053.
[4]
(h) Feng, X.; Xu, C.; Wang, Z.; Tang, S.; Fu, W.; Ji, B.; Wang, L. Inorg. Chem. 2015, 54, 2088.
[4]
(i) Yu, J.; Shen, M.; Lu, M. J. Iran. Chem. Soc. 2015, 12, 771.
[4]
(j) Prakash, G.; Ramachandran, R.; Nirmala, M.; Viswanathamurthi, P.; Linert, W. Monatsh. Chem. 2014, 145, 1903.
[4]
(k) Narang, U.; Yadav, K. K.; Bhattacharya, S.; Chauhan, S. M. S. ChemistrySelect 2017, 2, 7135.
[4]
(l) Li, J.; Liu, H.; Zhu, H.; Yao, W.; Wang, D. ChemCatChem 2021, 13, 4751.
[4]
(m) Yu, J.; Xu, J.; Lu, M. Appl. Organomet. Chem. 2013, 27, 606.
[4]
(n) Endo, Y.; B?ckvall, J. E. Chem.-Eur. J. 2012, 18, 13609.
[4]
(o) Li, J.; Yang, Y.; Hu, W.; Xia, X.; Wang, D. Chin. J. Org. Chem. 2022, 42, 190. (in Chinese)
[4]
( 李家豪, 杨义科, 胡文康, 夏晓峰, 王大伟, 有机化学, 2022, 42, 190.)
[4]
(p) Yu, H.; Wada, K.; Fukutake, T.; Feng, Q.; Uemura, S.; Isoda, K.; Hirai, T.; Iwamoto, S. Catal. Today 2021, 375, 410.
[4]
(q) Ramachandran, R.; Prakash, G.; Selvamurugan, S.; Viswanathamurthi, P.; Malecki, J. G.; Ramkumar, V. Dalton Trans. 2014, 43, 7889.
[4]
(r) Lai, Y. L.; Ye, J. S.; Huang, J. M. Chem.-Eur. J. 2016, 22, 5425.
[5]
(a) Cao, F.; Duan, Z.; Zhu, H.; Wang, D. Mol. Catal. 2021, 503, 111391.
[5]
(b) Khalili, D.; Banazadeh, A. R. Bull. Chem. Soc. Jpn. 2015, 88, 1693.
[5]
(c) Bains, A. K.; Dey, D.; Yadav, S.; Kundu, A.; Adhikari, D. Catal. Sci. Technol. 2020, 10, 6495.
[5]
(d) Liu, X.; Kuang, C.; Su, C. Acta Chim. Sinica 2022, 80, 1135. (in Chinese)
[5]
( 刘霞, 匡春香, 苏长会, 化学学报, 2022, 80, 1135.)
[5]
(e) Chakraborty, G.; Mondal, R.; Guin, A. K.; Paul, N. D. Org. Biomol. Chem. 2021, 19, 7217.
[5]
(f) Kaldhi, D.; Vodnala, N.; Gujjarappa, R.; Nayak, S.; Ravichandiran, V.; Gupta, S.; Hazra, C. K.; Malakar, C. C. Tetrahedron Lett. 2019, 60, 223.
[5]
(g) Li, J.; Mao, A.; Yao, W.; Zhu, H.; Wang, D. Green Chem. 2022, 24, 2602.
[5]
(h) Samanta, P. K.; Ray, S.; Das, T.; Gage, S. H.; Nandi, M.; Richards, R. M.; Biswas, P. Microporous Mesoporous Mater. 2019, 284, 186.
[5]
(i) Guang, R.; Zhao, H.; Zhang, M. Org. Lett. 2022, 24, 3048.
[5]
(j) Wilfred, C. D.; Taylor, R. J. K. Synlett 2004, 1628.
[5]
(k) Mohanty, A.; Roy, S. Tetrahedron Lett. 2016, 57, 2749.
[5]
(l) Liu, J.; Wang, C.; Ma, X.; Shi, X.; Wang, X.; Li, H.; Xu, Q. Catal. Lett. 2016, 146, 2139.
[5]
(m) Xu, Z.; Yu, X.; Sang, X.; Wang, D. Green Chem. 2018, 20, 2571.
[6]
(a) Das, K.; Waiba, S.; Jana, A.; Maji, B. Chem. Soc. Rev. 2022, 51, 4396.
[6]
(b) Borthakur, I.; Sau, A.; Kundu, S. Coordin. Chem. Rev. 2022, 451, 214257.
[6]
(c) Irrgang, T.; Kempe, R. Chem. Rev. 2019, 119, 2524.
[6]
(d) Wei, D.; Darcel, C. Chem. Rev. 2019, 119, 2550.
[6]
(e) Hey, D. A.; Reich, R. M.; Baratta, W.; Kühn, F. E. Chem. Rev. 2018, 374, 114.
[6]
(f) Corma, A.; Navas, J.; Sabater, M J Chem. Rev. 2018, 119 1410.
[6]
(g) Goyal, V.; Sarki, N.; Narani, A.; Naik, G.; Natte, K.; Jagadeesh, R. V. Coord. Chem. Rev. 2023, 474, 214827.
[6]
(h) Podyacheva, E.; Afanasyev, O. I.; Vasilyev, D. V.; Chusov, D. ACS Catal. 2022, 12, 7142.
[6]
(i) Tong, T.; Douthwaite, M.; Chen, L.; Engel, R.; Conway, M. B.; Guo, W.; Wu, X.; Gong, X.; Wang, Y.; Morgan, D. J.; Davies, T.; Kiely, C. J.; Chen, L.; Liu, X.; Hutchings, G. J. ACS Catal. 2023, 13, 1207.
[6]
(j) Wang, S.; Song, D.; Shen, F.; Chen, R.; Cheng, Y.; Zhao, C.; Shen, Q.; Yin, S.; Ling, F.; Zhong, W. Green Chem. 2023, 25, 357.
[6]
(k) Jin, M. Y.; Zhou, Y.; Xiao, D.; You, Y.; Zhen, Q.; Tao, G.; Yu, P.; Xing, X. Angew. Chem., Int. Ed. 2022, 61, e202112993.
[7]
Wu, M.; Hu, X.; Liu, J.; Liao, Y.; Deng, G. Org. Lett. 2012, 14, 2722.
[8]
Putta, R. R.; Chun, S.; Choi, S. H.; Lee, S. H.; Oh, D.; Hong, S. J. Org. Chem. 2020, 85, 15396.
[9]
Tang, L.; Guo, X.; Yang, Y.; Zha, Z.; Wang, Z. Chem. Commun. 2014, 50, 6145.
[10]
(a) Sen, C.; Sahoo, T.; Galani, S. M.; Panda, A. B.; Ghosh, S. C. ChemistrySelect 2016, 1, 2542.
[10]
(b) Chaurasia, S. R.; Bhanage, B. M. ChemistrySelect 2018, 3, 7963.
[11]
(a) Banerjee, R.; Phan, A.; Wang, B.; Knobler, C.; Furukawa, H.; O'Keeffe, M.; Yaghi, O. M. Science 2008, 319, 939.
[11]
(b) Banerjee, R.; Furukawa, H.; Britt, D.; Knobler, C.; O'Keeffe, M.; Yaghi, O. M. J. Am. Chem. Soc. 2009, 131, 3875.
[11]
(c) Chen, R.; Yao, J.; Gu, Q.; Smeets, S.; Baerlocher, C.; Gu, H.; Zhu, D.; Morris, W.; Yaghi, O. M.; Wang, H. Chem. Commun. 2013, 49, 95002.
[11]
(d) Jia, H.; Xie, R.; Lu, G.; Jiang, H.; Zhang, M. ACS Catal. 2022, 12, 10294.
[11]
(e) Feng, Y.; Wang, H.; Yao, J. Coord. Chem. Rev. 2021, 431, 213677.
[12]
(a) Zanon, A.; Verpoort, F. Coord. Chem. Rev. 2017, 353, 201.
[12]
(b) Cheng, N.; Ren, L.; Xu, X.; Du, Y.; Dou, S. X. Adv. Energy Mater. 2018, 8, 1801257.
[12]
(c) Duan, C.; Yu, Y.; Hu, H. Green Energy Environ. 2020, 29, 827.
[13]
(a) Ma, D.; Li, B.; Shi, Z. Chin. Chem. Lett. 2018, 29, 827.
[13]
(b) Qin, Y.; Li, Z.; Duan, Y.; Guo, J.; Zhao, M.; Tang, Z. Matter 2022, 5, 3260.
[13]
(c) Wang, Y.; Chen, L.; Hou, C. C.; Wei, Y. S.; Xu, Q. Org. Biomol. Chem. 2020, 18, 8508.
[14]
(a) Park, H.; Oh, S.; Lee, S.; Choi, S.; Oh, M. Appl. Catal., B 2019, 246, 322.
[14]
(b) Zhang, C.; Yang, H.; Zhong, D.; Xu, Y.; Wang, Y.; Yuan, Q.; Liang, Z.; Wang, B.; Zhang, W.; Zheng, H.; Cheng, T.; Cao, R. J. Mater. Chem. A 2020, 8, 9536.
[14]
(c) Guo, F.; He, Y.; Zeng, H.; Liu, H.; Yang, D.; Chen, H.; Li, H.; Liu, Y. Colloids Surf., A 2022, 648, 129417.
[15]
Zhang, J.; Zhang, T.; Yu, D.; Xiao, K.; Hong, Y. CrystEngComm 2015, 17, 8212.
[16]
Chen, M.; Peng, C.; Su, Y.; Chen, X.; Zhang, Y.; Wang, Y.; Peng, J. Angew. Chem., Int. Ed. 2020, 59, 20988.
[17]
Fu, H.; Wang, Z.; Wang, X.; Wang, P.; Wang, C. C. CrystEngComm 2018, 20, 1473.
[18]
(a) Hao, Y.; Sani, L, A.; Ge, T.; Fang, Q. Appl. Surf. Sci. 2017, 419, 826.
[18]
(b) Sun, X.; Xu, W.; Zhang, X.; Lei, T.; Lee, S. Y.; Wu, Q. J. Energy Chem. 2021, 52, 170.
[18]
(c) Ong, J. Y.; Ng, X. Q.; Lu, S.; Zhao, Y. Org. Lett. 2020, 22, 6447.
[18]
(d) He, J.; Jiao, L.; Cheng, X.; Chen, G.; Wu, Q.; Wang, X.; Yang, L.; Hu, Z. Acta Chim. Sinica 2022, 80, 896. (in Chinese)
[18]
( 何家伟, 焦柳, 程雪怡, 陈光海, 吴强, 王喜章, 杨立军, 胡征, 化学学报, 2022, 80, 896.)
[19]
(a) Sasikumar, B.; Arthanareeswaran, G. Appl. Surf. Sci. 2022, 606, 154900.
[19]
(b) Wang, D.; Hu, J.; Li, Y.; Fu, M.; Liu, D.; Chen, Q. J. Membr. Sci. 2016, 501, 228.
[20]
(a) Zárate-Guzmán, A. I.; González-Gutiérrez, L. V.; Ocampo-Pérez, R.; Carrasco-Marín, F.; Romero-Cano, L. A. J. Water Process Eng. 2020, 36, 101273.
[20]
(b) Gao, X.; Cao, Z.; Li, C.; Liu, J.; Liu, X.; Guo, L. New J. Chem. 2022, 46, 18952.
[21]
Liu, H.; Wei, G.; Xu, Z.; Liu, P.; Li, Y. Appl. Surf. Sci. 2016, 389, 438.
[22]
(a) Quintard, A.; Rodriguez, J. Angew. Chem. Int. Ed. 2014, 53, 4044.
[22]
(b) Yan, T.; Feringa, B. L.; Barta, K. Nat. Commun. 2014, 5, 5602.
[22]
(c) Quintard, A.; Constantieux, T.; Rodriguez, J. Angew. Chem., Int. Ed. 2013, 52, 12883.
[22]
(d) Pan, H. J.; Lin, Y.; Gao, T.; Lau, K. K.; Feng, W.; Yang, B.; Zhao, Y. Angew. Chem., Int. Ed. 2021, 133, 18747.
[22]
(e) Elangovan, S.; Sortais, J. B.; Beller, M.; Darcel, C. Angew. Chem., Int. Ed. 2015, 54, 14483.
[22]
(f) Polidano, K.; Allen, B. D. W.; Williams, J. M. J.; Morrill, L. C. ACS Catal. 2018, 8, 6440.
[22]
(g) Bettoni, L.; Gaillard, S.; Renaud, J. L. Org. Lett. 2020, 22, 2064.
[22]
(h) Chang, S.; Liu, H.; Shi, G.; Xia, X.; Wang, D.; Duan, Z. New J. Chem. 2022, 46, 15929.
[22]
(i) Bettoni, L.; Gaillard, S.; Renaud, J. L. Org. Lett. 2019, 21, 8404.
[22]
(j) Guo, N.; Zhu, S. Chin. J. Org. Chem. 2015, 35, 1383. (in Chinese)
[22]
( 郭娜, 朱守非, 有机化学, 2015, 35, 1383.)
[23]
(a) Singh, A. S.; Singh, M.; Mishra, N.; Mishra, S.; Agrahari, A. K.; Tiwari, V. K. ChemistrySelect 2017, 2, 154.
[23]
(b) Mishra, N.; Singh, A. S.; Agrahari, A. K.; Singh, S. K.; Singh, M.; Tiwari, V. K. ACS Appl. Energy Mater. 2019, 21, 389.
[23]
(c) Patra, A.; James, A.; Das, T. K.; Biju, A. T. J. Org. Chem. 2018, 83, 14820.
[23]
(d) Meeniga, I.; Gokanapalli, A.; Peddiahgari, V. G. R. Sustainable Chem. Pharm. 2022, 30, 100874.
[23]
(e) Boissarie, P. J.; Hamilton, Z. E.; Lang, S.; Murphy, J. A.; Suckling, C. J. Org. Lett. 2011, 13, 6256.
[23]
(f) Leng, Y.; Yang, F.; Zhu, W.; Zou, D.; Wu, Y.; Cai, R. Tetrahedron 2011, 67, 6191.
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