Strategies to Enhance the Photosensitization: Polymerization and the Donor–Acceptor Even–Odd Effect
Dr. Shunjie Liu
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and econstruction, Institute for Advanced Studgy and Department of Chemical and Biological Engineering, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
HKUST-Shenzhen Research Institute, No.9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen, 518057 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Haoke Zhang
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and econstruction, Institute for Advanced Studgy and Department of Chemical and Biological Engineering, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
HKUST-Shenzhen Research Institute, No.9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen, 518057 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Yuanyuan Li
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and econstruction, Institute for Advanced Studgy and Department of Chemical and Biological Engineering, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
HKUST-Shenzhen Research Institute, No.9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen, 518057 China
These authors contributed equally to this work.
Search for more papers by this authorJunkai Liu
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and econstruction, Institute for Advanced Studgy and Department of Chemical and Biological Engineering, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
HKUST-Shenzhen Research Institute, No.9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen, 518057 China
Search for more papers by this authorDr. Lili Du
Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong SAR, China
Institute of Life Sciences, Jiangsu University, Zhenjiang, 212013 China
Search for more papers by this authorDr. Ming Chen
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and econstruction, Institute for Advanced Studgy and Department of Chemical and Biological Engineering, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
HKUST-Shenzhen Research Institute, No.9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen, 518057 China
Search for more papers by this authorDr. Ryan T. K. Kwok
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and econstruction, Institute for Advanced Studgy and Department of Chemical and Biological Engineering, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
HKUST-Shenzhen Research Institute, No.9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen, 518057 China
Search for more papers by this authorDr. Jacky W. Y. Lam
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and econstruction, Institute for Advanced Studgy and Department of Chemical and Biological Engineering, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
HKUST-Shenzhen Research Institute, No.9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen, 518057 China
Search for more papers by this authorProf. David Lee Phillips
Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong SAR, China
Search for more papers by this authorCorresponding Author
Prof. Ben Zhong Tang
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and econstruction, Institute for Advanced Studgy and Department of Chemical and Biological Engineering, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
HKUST-Shenzhen Research Institute, No.9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen, 518057 China
Center for Aggregation-Induced Emission, SCUT-HKUST Joint Research Institute, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640 China
Search for more papers by this authorDr. Shunjie Liu
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and econstruction, Institute for Advanced Studgy and Department of Chemical and Biological Engineering, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
HKUST-Shenzhen Research Institute, No.9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen, 518057 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Haoke Zhang
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and econstruction, Institute for Advanced Studgy and Department of Chemical and Biological Engineering, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
HKUST-Shenzhen Research Institute, No.9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen, 518057 China
These authors contributed equally to this work.
Search for more papers by this authorDr. Yuanyuan Li
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and econstruction, Institute for Advanced Studgy and Department of Chemical and Biological Engineering, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
HKUST-Shenzhen Research Institute, No.9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen, 518057 China
These authors contributed equally to this work.
Search for more papers by this authorJunkai Liu
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and econstruction, Institute for Advanced Studgy and Department of Chemical and Biological Engineering, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
HKUST-Shenzhen Research Institute, No.9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen, 518057 China
Search for more papers by this authorDr. Lili Du
Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong SAR, China
Institute of Life Sciences, Jiangsu University, Zhenjiang, 212013 China
Search for more papers by this authorDr. Ming Chen
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and econstruction, Institute for Advanced Studgy and Department of Chemical and Biological Engineering, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
HKUST-Shenzhen Research Institute, No.9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen, 518057 China
Search for more papers by this authorDr. Ryan T. K. Kwok
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and econstruction, Institute for Advanced Studgy and Department of Chemical and Biological Engineering, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
HKUST-Shenzhen Research Institute, No.9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen, 518057 China
Search for more papers by this authorDr. Jacky W. Y. Lam
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and econstruction, Institute for Advanced Studgy and Department of Chemical and Biological Engineering, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
HKUST-Shenzhen Research Institute, No.9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen, 518057 China
Search for more papers by this authorProf. David Lee Phillips
Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong SAR, China
Search for more papers by this authorCorresponding Author
Prof. Ben Zhong Tang
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and econstruction, Institute for Advanced Studgy and Department of Chemical and Biological Engineering, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China
HKUST-Shenzhen Research Institute, No.9 Yuexing 1st RD, South Area, Hi-tech Park, Nanshan, Shenzhen, 518057 China
Center for Aggregation-Induced Emission, SCUT-HKUST Joint Research Institute, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou, 510640 China
Search for more papers by this authorGraphical Abstract
Conjugated polymers have a higher 1O2 generation efficiency than their small molecular counterparts. Photosensitizers with A-D-A structures are better than D-A-D structures. Both in vitro and in vivo experiments show that the resulting materials can be used as photosensitizers in image-guided photodynamic anticancer therapy. D=donor, A=acceptor.
Abstract
A particular challenge in the design of organic photosensitizers (PSs) with donor–acceptor (D-A) structures is that it is based on trial and error rather than specific rules. Now these challenges are addressed by proposing two efficient strategies to enhance the photosensitization efficiency: polymerization-facilitated photosensitization and the D-A even–odd effect. Conjugated polymers have been found to exhibit a higher 1O2 generation efficiency than their small molecular counterparts. Furthermore, PSs with A-D-A structures show enhanced photosensitization efficiency over those with D-A-D structures. Theoretical calculations suggest an enhanced intersystem crossing (ISC) efficiency by these strategies. Both in vitro and in vivo experiments demonstrate that the resulting materials can be used as photosensitizers in image-guided photodynamic anticancer therapy. These guidelines are applicable to other polymers and small molecules to lead to the development of new PSs.
Supporting Information
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References
- 1
- 1aJ. Ge, M. Lan, B. Zhou, W. Liu, L. Guo, H. Wang, Q. Jia, G. Niu, X. Huang, H. Zhou, X. Meng, P. Wang, C.-S. Lee, W. Zhang, X. Han, Nat. Commun. 2014, 5, 4596;
- 1bD. E. Dolmans, D. Fukumura, R. K. Jain, Nat. Rev. Cancer 2003, 3, 380;
- 1cC. M. Moore, D. Pendse, M. Emberton, Nat. Rev. Urology 2009, 6, 18;
- 1dA. P. Castano, P. Mroz, M. R. Hamblin, Nat. Rev. Cancer 2006, 6, 535;
- 1eW. Wenting, S. Xiaodong, Z. Jianzhang, W. Mingbo, Adv. Sci. 2017, 4, 1700113;
- 1fZ. Zhou, J. Song, L. Nie, X. Chen, Chem. Soc. Rev. 2016, 45, 6597–6626.
- 2
- 2aJ. F. Lovell, T. W. Liu, J. Chen, G. Zheng, Chem. Rev. 2010, 110, 2839–2857;
- 2bS. Singh, A. Aggarwal, N. V. S. D. K. Bhupathiraju, G. Arianna, K. Tiwari, C. M. Drain, Chem. Rev. 2015, 115, 10261–10306;
- 2cM. Ethirajan, Y. Chen, P. Joshi, R. K. Pandey, Chem. Soc. Rev. 2011, 40, 340–362.
- 3
- 3aD. Wang, H. Su, R. T. K. Kwok, X. Hu, H. Zou, Q. Luo, M. S. Lee, W. Xu, J. W. Y. Lam, B. Z. Tang, Chem. Sci. 2018, 9, 3685–3693;
- 3bZ. Zheng, T. Zhang, H. Liu, Y. Chen, R. T. K. Kwok, C. Ma, P. Zhang, H. H. Y. Sung, I. D. Williams, J. W. Y. Lam, K. S. Wong, B. Z. Tang, ACS Nano 2018, 12, 8145–8159;
- 3cM. Jiang, R. T. Kwok, X. Li, C. Gui, J. W. Lam, J. Qu, B. Z. Tang, J. Mater. Chem. B 2018, 6, 2557–2565;
- 3dW. Wu, D. Mao, F. Hu, S. Xu, C. Chen, C.-J. Zhang, X. Cheng, Y. Yuan, D. Ding, D. Kong, B. Liu, Adv. Mater. 2017, 29, 1700548.
- 4
- 4aJ. Mei, N. L. C. Leung, R. T. K. Kwok, J. W. Y. Lam, B. Z. Tang, Chem. Rev. 2015, 115, 11718–11940;
- 4bS. Liu, Y. Cheng, H. Zhang, Z. Qiu, R. T. Kwok, J. W. Lam, B. Z. Tang, Angew. Chem. Int. Ed. 2018, 57, 6274–6278; Angew. Chem. 2018, 130, 6382–6386;
- 4cL. Ma, X. Feng, S. Wang, B. Wang, Mater. Chem. Front. 2017, 1, 2474–2486;
- 4dQ. Wan, R. Jiang, L. Mao, D. Xu, G. Zeng, Y. Shi, F. Deng, M. Liu, X. Zhang, Y. Wei, Mater. Chem. Front. 2017, 1, 1051–1058.
- 5X. Gu, X. Zhang, H. Ma, S. Jia, P. Zhang, Y. Zhao, Q. Liu, J. Wang, X. Zheng, J. W. Y. Lam, D. Ding, B. Z. Tang, Adv. Mater. 2018, 30, 1801065.
- 6F. Hu, S. Xu, B. Liu, Adv. Mater. 2018, 30, 1801350.
- 7S. Xu, Y. Yuan, X. Cai, C.-J. Zhang, F. Hu, J. Liang, G. Zhang, D. Zhang, B. Liu, Chem. Sci. 2015, 6, 5824–5830.
- 8K. Schmidt, S. Brovelli, V. Coropceanu, D. Beljonne, J. Cornil, C. Bazzini, T. Caronna, R. Tubino, F. Meinardi, Z. Shuai, J.-L. Brédas, J. Phys. Chem. A 2007, 111, 10490–10499.
- 9
- 9aT. Yogo, Y. Urano, Y. Ishitsuka, F. Maniwa, T. Nagano, J. Am. Chem. Soc. 2005, 127, 12162–12163;
- 9bR. Acharya, S. Cekli, C. J. Zeman IV, R. M. Altamimi, K. S. Schanze, J. Phys. Chem. Lett. 2016, 7, 693–697;
- 9cS. Cekli, R. W. Winkel, E. Alarousu, O. F. Mohammed, K. S. Schanze, Chem. Sci. 2016, 7, 3621–3631;
- 9dJ. Zhao, W. Wu, J. Sun, S. Guo, Chem. Soc. Rev. 2013, 42, 5323–5351.
- 10S. Cekli, R. W. Winkel, K. S. Schanze, J. Phys. Chem. A 2016, 120, 5512–5521.
- 11S. H. Lim, C. Thivierge, P. Nowak-Sliwinska, J. Han, H. van den Bergh, G. Wagnières, K. Burgess, H. B. Lee, J. Med. Chem. 2010, 53, 2865–2874.
- 12
- 12aY. Xiong, Z. Zhao, W. Zhao, H. Ma, Q. Peng, Z. He, X. Zhang, Y. Chen, X. He, J. W. Y. Lam, B. Z. Tang, Angew. Chem. Int. Ed. 2018, 57, 7997–8001; Angew. Chem. 2018, 130, 8129–8133;
- 12bH. Tsujimoto, D.-G. Ha, G. Markopoulos, H. S. Chae, M. A. Baldo, T. M. Swager, J. Am. Chem. Soc. 2017, 139, 4894–4900;
- 12cW. Zhao, Z. He, Q. Peng, J. W. Y. Lam, H. Ma, Z. Qiu, Y. Chen, Z. Zhao, Z. Shuai, Y. Dong, B. Z. Tang, Nat. Commun. 2018, 9, 3044.
- 13S. Xu, W. Wu, X. Cai, C.-J. Zhang, Y. Yuan, J. Liang, G. Feng, P. Manghnani, B. Liu, Chem. Commun. 2017, 53, 8727–8730.
- 14While this Communication was under review, a manuscript was published detailing the polymerization-enhanced photosensitization: W. Wu, D. Mao, S. Xu, Kenry, F. Hu, X. Li, D. Kong, B. Liu, Chem 2018, 4, 1937–1951.
- 15R. Magyar, S. Tretiak, Y. Gao, H.-L. Wang, A. Shreve, Chem. Phys. Lett. 2005, 401, 149–156.
- 16
- 16aW. Qin, D. Ding, J. Z. Liu, W. Z. Yuan, Y. Hu, B. Liu, B. Z. Tang, Adv. Funct. Mater. 2012, 22, 771–779;
- 16bW. Qin, K. Li, G. Feng, M. Li, Z. Yang, B. Liu, B. Z. Tang, Adv. Funct. Mater. 2014, 24, 635–643.
- 17J. Cornil, D. A. dos Santos, X. Crispin, R. Silbey, J. L. Brédas, J. Am. Chem. Soc. 1998, 120, 1289–1299.
- 18M. Ochsner, J. Photochem. Photobiol. B 1997, 39, 1–18.
- 19X. Han, Q. Bai, L. Yao, H. Liu, Y. Gao, J. L, L. Liu, Y. Liu, X. Li, P. Lu, B. Yang, Adv. Funct. Mater. 2015, 25, 7521–7529.
- 20Y. Wang, M. Chen, N. Alifu, S. Li, W. Qin, A. Qin, B. Z. Tang, J. Qian, ACS Nano 2017, 11, 10452–10461.
- 21R. W. Horobin, S. Trapp, V. Weissig, J. Controlled Release 2007, 121, 125–136.
- 22C.-J. Zhang, Q. Hu, G. Feng, R. Zhang, Y. Yuan, X. Lu, B. Liu, Chem. Sci. 2015, 6, 4580–4586.
- 23J. Shi, P. W. Kantoff, R. Wooster, O. C. Farokhzad, Nat. Rev. Cancer 2017, 17, 20.
- 24J.-H. Park, L. Gu, G. Von Maltzahn, E. Ruoslahti, S. N. Bhatia, M. J. Sailor, Nat. Mater. 2009, 8, 331.