Intramolecular Charge Transfer-Enhanced BODIPY Photosensitizer in Photoinduced Electron Transfer and Its Application to Photoxidation under Mild Condition
Ruiqin Wang
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China
Search for more papers by this authorYing Geng
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China
Search for more papers by this authorLili Zhang
Science and Techology Bureau of Huangdao, Qingdao, Shandong 266400, China
Search for more papers by this authorCorresponding Author
Wenting Wu
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China, Tel.: 0086-0532-86984615Search for more papers by this authorWeiyu Fan
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China
Search for more papers by this authorZhongtao Li
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China
Search for more papers by this authorLizhuo Wang
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China
Search for more papers by this authorLiying Zhan
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China
Search for more papers by this authorXueyan Wu
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China
Search for more papers by this authorCorresponding Author
Mingbo Wu
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China, Tel.: 0086-0532-86984615Search for more papers by this authorRuiqin Wang
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China
Search for more papers by this authorYing Geng
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China
Search for more papers by this authorLili Zhang
Science and Techology Bureau of Huangdao, Qingdao, Shandong 266400, China
Search for more papers by this authorCorresponding Author
Wenting Wu
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China, Tel.: 0086-0532-86984615Search for more papers by this authorWeiyu Fan
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China
Search for more papers by this authorZhongtao Li
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China
Search for more papers by this authorLizhuo Wang
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China
Search for more papers by this authorLiying Zhan
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China
Search for more papers by this authorXueyan Wu
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China
Search for more papers by this authorCorresponding Author
Mingbo Wu
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China
State Key Laboratory of Heavy Oil Processing, School of Chemical Engineering, China University of Petroleum, Qingdao, Shandong 266580, China, Tel.: 0086-0532-86984615Search for more papers by this authorAbstract
Photoinduced electron transfer process is a crucial step in photooxidation to obtain synthetic chemicals. However, the driving forces of electron transfer as priority in all have been rarely studied in stepwise detail. Herein, we report a series of BODIPY derivatives with an emphasis on the intramolecular charge transfer, enhancing the key step of photoinduced electron transfer process and photooxidation performances. A series of novel BODIPY photosensitizers (B-1–B-5) were prepared, wherein diethylamine amino of B-3 as charge injection group was conjugated to the 2,6-diiodo-styryl-BODIPY, and the electron transfer impetus was enhanced 1.6 times due to its more negative redox potentials. These results were also confirmed by the DFT/TDDFT calculation. Without pure oxygen, B-3 still can exhibit an exceptional performance in photoxidative aromatization of 1,4-DHP under mild condition. After irradiation for 28 min, the conversion rate came to 98.2%.
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REFERENCES
- 1 Hirakawa, T.; Yawata, K.; Nosaka, Y.. Appl. Catal. A-Gen., 2007, 1, 105.
- 2 Nilushika, D.; Awad, M.-I.; Saleh, M.-M.; Okajima, T.; Mao, L.; Ohsaka, T.. Chem. Commun., 2015, 16, 3343.
- 3 Wada, A.; Jitsukawa, K.; Masuda, H.. Angew. Chem., Int. Ed., 2013, 47, 125.
- 4
Hintz, S.;
Mattay, J.;
Eldik, R.;
Fu, W..
Eur. J. Org. Chem.,
1998,
8,
1583.
10.1002/(SICI)1099-0690(199808)1998:8<1583::AID-EJOC1583>3.0.CO;2-R Google Scholar
- 5 Huang, L.; Zhao, J.-Z.. RSC Adv., 2013, 45, 23377.
- 6 Bozdemir, O.-A.; Guliyev, R.; Buyukcakir, O.; Selcuk, S.; Kolemen, S.; Gulseren, G.; Nalbantoglu, T.; Boyaci, H.; Akkaya, E.-U.. J. Am. Chem. Soc., 2010, 132, 8029.
- 7 Hirakawa, T.; Nosaka, Y.. J. Phys. Chem. C, 2008, 40, 15818.
- 8 Fang, X.; Liu, Y.-C.; Li, C.. J. Org. Chem., 2007, 22, 8608.
- 9 Barata-Vallejo, S.; Flesia, M.-M.; Lantaño, B.; Argüello, J.-E.; Peñéñory, A.-B.; Postigo, A.. Eur. J. Org. Chem., 2013, 5, 998.
- 10 Fukuzumi, S.; Yamada, Y.; Suenobu, T.; Ohkubo, K.; Kotani, H.. Energ. Environ. Sci., 2011, 8, 2754.
- 11 Harriman, A.; Sauvage, J.-P.-A.. Chem. Soc. Rev., 1996, 1, 41.
- 12 Ma, X.; Azeem, E.-A.; Liu, X.; Cheng, Y.; Zhu, C.. J. Mater. Chem. C, 2014, 6, 1076.
- 13 Guldi, D.-M.; Gouloumis, A.; Vázquez, P.; Torres, T.. Chem. Commun., 2002, 2056.
- 14 Erten, E.-S.; Yilmaz, M.-D.; Icli, B.; Dede, Y.; Icli, S.; Akkaya, E.-U.. Org. Lett., 2008, 15, 3299.
- 15 Pelado, B.; Abou-Chahine, F.; Calbo, J.; Caballero, R.; Cruz, P.-D.-L.; Junquera-Hernández, J.-M.; Enrique, O.; Nikolai, V.-T.; Langa, F.. Chem. Eur. J., 2015, 15, 5814.
- 16 Nascimento, S.; Fedorov, A.; Brites, M.-J.; Berberan-Santos, M.-N.. Dyes Pigments, 2015, 114, 158.
- 17 Pfattner, R.; Pavlica, E.; Jaggi, M.; Liu, S.-X.; Decurtins, S.; Bratina, G.; Veciana, J.; Mas-Torrent, M.; Rovira, C.. J. Mater. Chem. C, 2013, 25, 3985.
- 18 Ley, D.; Guzman, C.-X.; Adolfsson, K.-H.; Scott, A.-M.; Brausc- hweig, A.-B.. J. Am. Chem. Soc., 2014, 22, 7809.
- 19 Joachim, K.; Robert, S.; Maria, W.; Ulrich, S.-S.; Benjamin, D.; Michael, J.. J. Phys. Chem. C, 2015, 9, 4742.
- 20 Gunderson, V.-L.; Krieg, E.; Vagnini, M.-T.; Iron, M.-A.; Rybtchins- ki, B.; Wasielewski, M.-R.. J. Phys. Chem. B, 2011, 23, 7533.
- 21 Sato, T.; Nozawa, S.; Tomita, A.; Hoshino, M.; Koshihara, S.-Y.; Fujii, H.. J. Phys. Chem. C, 2012, 27, 14232.
- 22 Liu, S.-J.; Lin, W.-P.; Yi, M.-D.; Xu, W.-J.; Tang, C.; Zhao, Q.; Ye, S.-H.; Liu, X.-M.; Huang, W.. J. Mater. Chem., 2012, 43, 22964.
- 23 Wenger, O.-S.. Coordin. Chem. Rev., 2015, 282, 150.
- 24a Lin, X.-H.; Li, S.-F.-Y.. Appl. Catal. B Environ., 2015, 170, 263.
- 24b Guillard, C.; Disdier, J.; Herrmann, J.-M.; Lehaut, C.; Chopin, T.; Malato, S.; Blanco, J.. Catal. Today, 1999, 2, 217.
- 25a Gaya, U.-I.; Abdullah, A.-H.. J. Photochem. Photobiol. C, 2008, 1, 1.
- 25b Li, Y.; Wen, B.; Yu, C.; Chen, C.; Ji, H.; Ma, W.; Zhao, J.. Chem. Eur. J., 2012, 1, 2030.
- 26 Tian, C.; Zhang, Q.; Wu, A.; Jiang, M.; Liang, Z.; Jiang, B.; Fu, H.. Chem. Commun., 2012, 23, 2858.
- 27 Choina, J.; Bagabas, A.; Fischer, C.; Flechsig, G.-U.; Kosslick, H.; Alshammari, A.; Schulz, A.. Catal. Today, 2015, 241, 47.
- 28a Weber, A.-S.; Grady, A.-M.; Koodali, R.-T.. Catal. Sci. Technol., 2012, 4, 683.
- 28b Tada, H.; Kiyonaga, T.; Naya, S.. Chem. Soc. Rev., 2009, 7, 1849.
- 29a Wang, Y.; Bai, X.; Pan, C.; He, J.; Zhu, Y.. J. Mater. Chem., 2012, 23, 11568.
- 29b Fu, H.; Zhang, L.; Yao, W.; Zhu, Y.. Appl. Catal. B, 2006, 1, 100.
- 30 Ravelli, D.; Dondi, D.; Fagnoni, M.; Albini, A.. Chem. Soc. Rev., 2009, 7, 1999.
- 31 Marin, M.-L.; Santos-Juanes, L.; Arques, A.; Amat, A.-M.; Miranda, M.-A.. Chem. Rev., 2012, 3, 1710.
- 32 Erbas-Cakmak, S.; Cakmak, F.-P.; Topel, S.-D.; Uyar, T.-B.; Akkaya, E.-U.. Chem. Commun., 2015, 61, 12258.
- 33 Zhou, Y.; Zhou, Z.; Li, Y.; Yang, W.. Catal. Commun., 2015, 64, 96.
- 34 Kamkaew, A.; Lim, S.-H.; Lee, H.-B.; Kiew, L.-V.; Chung, L.-Y.; Burgess, K.. Chem. Soc. Rev., 2013, 1, 77.
- 35 Caruso, E.; Banfi, S.; Barbieri, P.; Leva, B.; Orlandi, V.-T.. J. Photochem. Photobiol. B, 2012, 114, 44.
- 36 Banfi, S.; Caruso, E.; Zaza, S.; Mancini, M.; Marzia, B.-G.; Monti, E.. J. Photochem. Photobiol. B, 2012, 114, 52.
- 37a Orlandi, V.-T.; Rybtke, M.; Caruso, E.; Banfi, S.; Tolker, N.-T.; Barbieri, P.. Biofouling, 2014, 30, 883.
- 37b Banfi, S.; Nasini, G.; Zaza, S.; Caruso, E.. Tetrahedron, 2013, 69, 4845.
