Visible light responsive spiropyran derivatives based on dynamic coordination bonds
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* Corresponding author.
E-mail address: chli@nju.edu.cn (C.-H. Li).
1 These authors contributed equally to this work.
Citation: Xiong Xiao, Wei Zheng, Yue Zhao, Cheng-Hui Li. Visible light responsive spiropyran derivatives based on dynamic coordination bonds[J]. Chinese Chemical Letters, ;2023, 34(2): 107457. doi: 10.1016/j.cclet.2022.04.055
J. Zhang, Y. Fu, H.H. Han, et al., Nat. Commun. 8(2017) 987.
doi: 10.1038/s41467-017-01137-8
Y. Xiong, P. Rivera-Fuentes, E. Sezgin, et al., Org. Lett. 18(2016) 3666–3669.
doi: 10.1021/acs.orglett.6b01717
J. Yan, L.X. Zhao, C. Li, et al., J. Am. Chem. Soc. 137(2015) 2436–2439.
doi: 10.1021/ja512189a
X. Chai, H.H. Han, A.C. Sedgwick, et al., J. Am. Chem. Soc. 142(2020) 18005–18013.
doi: 10.1021/jacs.0c05379
L. Ming, L.Y. Gu, Q. Zhang, M.Z. Xue, Y.G. Liu, Chin. Chem. Lett. 24(2013) 1014–1018.
doi: 10.1016/j.cclet.2013.07.001
X. Tian, J. Li, Y. Zhang, et al., Sens. Actuator. B: Chem. 359(2022) 131618.
doi: 10.1016/j.snb.2022.131618
S. Son, E. Shin, B.S. Kim, Biomacromolecules 15(2014) 628–634.
doi: 10.1021/bm401670t
A. Fagan, M. Bartkowski, S. Giordani, Front. Chem. 9(2021) 720087.
doi: 10.3389/fchem.2021.720087
R. Klajn, Chem. Soc. Rev. 43(2014) 148–184.
doi: 10.1039/C3CS60181A
Y. Hao, J. Meng, S. Wang, Chin. Chem. Lett. 28(2017) 2085–2091.
doi: 10.1016/j.cclet.2017.10.019
B. Champagne, A. Plaquet, J.L. Pozzo, V. Rodriguez, F. Castet, J. Am. Chem. Soc. 134(2012) 8101–8103.
doi: 10.1021/ja302395f
A.A. Ali, R. Kharbash, Y. Kim, Anal. Chim. Acta 1110(2020) 199–223.
doi: 10.1016/j.aca.2020.01.057
L. Kortekaas, W.R. Browne, Chem. Soc. Rev. 48(2019) 3406–3424.
doi: 10.1039/C9CS00203K
M. Natali, S. Giordani, Chem. Soc. Rev. 41(2012) 4010–4029.
doi: 10.1039/c2cs35015g
L. Wang, Y. Liu, X. Zhan, D. Luo, X. Sun, J. Mater. Chem. C 7(2019) 8649–8654.
doi: 10.1039/C9TC02076D
J. Tian, J. Xu, H. Peng, et al., Prog. Org. Coat. 160(2021) 106531.
doi: 10.1016/j.porgcoat.2021.106531
L. Wimberger, S.K.K. Prasad, M.D. Peeks, et al., J. Am. Chem. Soc. 143(2021) 20758–20768.
doi: 10.1021/jacs.1c08810
Z. Shi, P. Peng, D. Strohecker, Y. Liao, J. Am. Chem. Soc. 133(2011) 14699–14703.
doi: 10.1021/ja203851c
M.J. Feeney, S.W. Thomas, Macromolecules 51(2018) 8027–8037.
doi: 10.1021/acs.macromol.8b01915
Y. Ma, Y. Yu, J. Li, et al., InfoMat 3(2021) 82–100.
doi: 10.1002/inf2.12125
T. Qin, J. Han, Y. Geng, et al., Chem. Eur. J. 24(2018) 12539–12545.
doi: 10.1002/chem.201801692
H. Zhang, Q. Li, Y. Yang, X. Ji, J.L. Sessler, J. Am. Chem. Soc. 143(2021) 18635–18642.
doi: 10.1021/jacs.1c08558
J. He, Y. Yang, Y. Li, et al., Cell Rep. Phys. Sci. 2(2021) 100643.
doi: 10.1016/j.xcrp.2021.100643
Q. Qi, C. Li, X. Liu, et al., J. Am. Chem. Soc. 139(2017) 16036–16039.
doi: 10.1021/jacs.7b07738
N.A. Voloshin, E.V. Solov'eva, S.O. Bezugliy, A.V. Metelitsa, V.I. Minkin, Chem. Heterocycl. Com. 48(2012) 1361–1370.
doi: 10.1007/s10593-012-1145-5
H. Wu, D. Zhang, L. Su, et al., J. Am. Chem. Soc. 129(2007) 6839–6846.
doi: 10.1021/ja0702824
L.X. Yu, Y. Liu, S.C. Chen, Y. Guan, Y.Z. Wang, Chin. Chem. Lett. 25(2014) 389–396.
doi: 10.1016/j.cclet.2013.12.014
L.N. Fu, B. Leng, Y.S. Li, X.K. Gao, Chin. Chem. Lett. 27(2016) 1319–1329.
doi: 10.1016/j.cclet.2016.06.045
C. Ventura, P. Thornton, S. Giordani, A. Heise, Polym. Chem. 5(2014) 6318–6324.
doi: 10.1039/C4PY00778F
M. Tomasulo, E. Deniz, R.J. Alvarado, F.M. Raymo, J. Phys. Chem. C 112(2008) 8038–8045.
M. Sommer, Macromol. Rapid Commun. 42(2021) e2000597.
doi: 10.1002/marc.202000597
N. Nadir, Z. Wahid, M.T. Zainuddin, N.Z. Mohamed Islam, Adv. Mater. Res. 925(2014) 323–328.
doi: 10.4028/www.scientific.net/AMR.925.323
E.I. Balmond, B.K. Tautges, A.L. Faulkner, et al., J. Org. Chem. 81(2016) 8744–8758.
doi: 10.1021/acs.joc.6b01193
J.Q. Ren, H. Tian, Sensors 7(2007) 3166–3178.
doi: 10.3390/s7123166
M. Natali, L. Soldi, S. Giordani, Tetrahedron 66(2010) 7612–7617.
doi: 10.1016/j.tet.2010.07.035
M. Baldrighi, G. Locatelli, J. Desper, C.B. Aakeroy, S. Giordani, Chem. Eur. J. 22(2016) 13976–13984.
doi: 10.1002/chem.201602608
T.J. Feuerstein, R. Muller, C. Barner-Kowollik, P.W. Roesky, Inorg. Chem. 58(2019) 15479–15486.
doi: 10.1021/acs.inorgchem.9b02547
I. Kim, D.C. Jeong, M. Lee, et al., Tetrahedron Lett. 56(2015) 6080–6084.
doi: 10.1016/j.tetlet.2015.09.055
N. Shao, J.Y. Jin, H. Wang, et al., Anal. Chem. 80(2008) 3466–3475.
doi: 10.1021/ac800072y
J.F. Zhu, H. Yuan, W.H. Chan, A.W. Lee, Org. Biomol. Chem. 8(2010) 3957–3964.
doi: 10.1039/c004871b
Y. Zhang, N. Shao, R. Yang, et al., Sci. China Ser. B 49(2006) 246–255.
doi: 10.1007/s11426-006-0246-3
G. Ma, Q. Zhou, X. Zhang, Y. Xu, H. Liu, New J. Chem. 38(2014) 552–560.
doi: 10.1039/C3NJ01238G
S. Goswami, A.K. Das, A.K. Maity, et al., Dalton Trans. 43(2014) 231–239.
doi: 10.1039/C3DT51851E
G.M. Sylvia, A.M. Mak, S. Heng, et al., Chemosensors 6(2018) 17.
doi: 10.3390/chemosensors6020017
D.B. Stubing, S. Heng, A.D. Abell, Org. Biomol. Chem. 14(2016) 3752–3757.
doi: 10.1039/C6OB00468G
Y. Shiraishi, Y. Matsunaga, T. Hirai, Chem. Commun. 48(2012) 5485–5487.
doi: 10.1039/c2cc30258f
J. Meng, H. Xu, Z. Li, S. Xu, C. Yao, Tetrahedron 73(2017) 6637–6643.
doi: 10.1016/j.tet.2017.10.014
X. Guo, D. Zhang, D. Zhu, Adv. Mater. 16(2004) 125–130.
doi: 10.1002/adma.200306102
T. Zhou, Z. Li, J. Wang, New J. Chem. 43(2019) 8869–8872.
doi: 10.1039/C9NJ01727E
F.B. Miguez, I.F. Reis, L.P. Dutra, et al., Dyes Pigments 171(2019) 107757.
doi: 10.1016/j.dyepig.2019.107757
D. Bleger, S. Hecht, Angew. Chem. Int. Ed. 54(2015) 11338–11349.
doi: 10.1002/anie.201500628
D. Roke, C. Stuckhardt, W. Danowski, S.J. Wezenberg, B.L. Feringa, Angew. Chem. Int. Ed. 57(2018) 10515–10519.
doi: 10.1002/anie.201802392
S. Helmy, F.A. Leibfarth, S. Oh, et al., J. Am. Chem. Soc. 136(2014) 8169–8172.
doi: 10.1021/ja503016b
A. Bagheri, C. Bainbridge, J. Jin, ACS Appl. Polym. Mater. 1(2019) 1896–1904.
doi: 10.1021/acsapm.9b00458
N.D. Shepherd, T. Wang, B. Ding, J.E. Beves, D.M. D'Alessandro, Inorg. Chem. 60(2021) 11706–11710.
doi: 10.1021/acs.inorgchem.0c03383
Y. Duan, H. Zhao, C. Xiong, et al., Chin. J. Chem. 39(2021) 985–998.
doi: 10.1002/cjoc.202000532
C.C. Ko, V.W. Yam, Acc. Chem. Res. 51(2018) 149–159.
doi: 10.1021/acs.accounts.7b00426
H.T. Sun, X.H. Tian, J. Autschbach, et al., J. Mater. Chem. C 1(2013) 5779–5790.
doi: 10.1039/c3tc31131g
J. -. X. Wang, C. Li, H. Tian, Coord. Chem. Rev. 427(2021) 213579.
doi: 10.1016/j.ccr.2020.213579
J. Lee, M.M. Sroda, Y. Kwon, et al., ACS Appl. Mater. Interfaces 12(2020) 54075–54082.
doi: 10.1021/acsami.0c15116
W. Qiu, P.A. Gurr, G.G. Qiao, ACS Appl. Mater. Interfaces 11(2019) 29268–29275.
doi: 10.1021/acsami.9b09023
T. Yamaguchi, A. Maity, V. Polshettiwar, M. Ogawa, Inorg. Chem. 57(2018) 3671–3674.
doi: 10.1021/acs.inorgchem.7b03132
W. Maret, Y. Li, Chem. Rev. 109(2009) 4682–4707.
doi: 10.1021/cr800556u
J.C. Lai, L. Li, D.P. Wang, et al., Nat. Commun. 9(2018) 2725.
doi: 10.1038/s41467-018-05285-3
J.C. Lai, X.Y. Jia, D.P. Wang, et al., Nat. Commun. 10(2019) 1164.
doi: 10.1038/s41467-019-09130-z
M. Schulz-Senft, P.J. Gates, F.D. Sönnichsen, A. Staubitz, Dyes Pigments 136(2017) 292–301.
doi: 10.1016/j.dyepig.2016.08.039
Y. Zhao, Z. Li, J. Ma, Q. Jia, ACS Appl. Mater. Interfaces 13(2021) 55806–55814.
doi: 10.1021/acsami.1c14739
Z. Wu, Q. Wang, P. Li, B. Fang, M. Yin, J. Mater. Chem. C 9(2021) 6290–6296.
doi: 10.1039/D1TC00974E
J.K. Rad, A.R. Mahdavian, H. Salehi-Mobarakeh, A. Abdollahi, Macromolecules 49(2015) 141–152.
M. Natali, C. Aakeroy, J. Desper, S. Giordani, Dalton Trans. 39(2010) 8269–8277.
doi: 10.1039/c0dt00242a
G. Berkovic, V. Krongauz, V. Weiss, Chem. Rev. 100(2000) 1741–1754.
doi: 10.1021/cr9800715
W. Szymanski, J.M. Beierle, H.A. Kistemaker, W.A. Velema, B.L. Feringa, Chem. Rev. 113(2013) 6114–6178.
doi: 10.1021/cr300179f
C. Heinzmann, S. Coulibaly, A. Roulin, G.L. Fiore, C. Weder, ACS Appl. Mater. Interfaces 6(2014) 4713–4719.
doi: 10.1021/am405302z
D. Habault, H. Zhang, Y. Zhao, Chem. Soc. Rev. 42(2013) 7244–7256.
doi: 10.1039/c3cs35489j
C.H. Li, J.L. Zuo, Adv. Mater. 32(2020) e1903762.
G. Li, Z. Pan, Z. Jia, et al., New J. Chem. 45(2021) 6386–6396.
doi: 10.1039/D1NJ00429H
A. Ahmad, Y. Wei, F. Syed, et al., RSC Adv. 5(2015) 99364–99377.
doi: 10.1039/C5RA20096B
S. Lee, J.E. Kwon, J. Hong, S.Y. Park, K. Kang, J. Mater. Chem. A 7(2019) 11438–11443.
doi: 10.1039/C9TA01508F
J. Boelke, S. Hecht, Adv. Opt. Mater. 7(2019) 1900404.
doi: 10.1002/adom.201900404
Y. Xiao, C. Cao, J. Coord. Chem. 71(2018) 3836–3846.
doi: 10.1080/00958972.2018.1540780
S.S. Deshpande, M.A. Jachak, S.S. Khopkar, G.S. Shankarling, Sens. Actuator B: Chem. 258(2018) 648–656.
doi: 10.1016/j.snb.2017.11.138
A. Kumar, S. Kumar, J. Photoch. Photobio. A 390(2020) 112265.
doi: 10.1016/j.jphotochem.2019.112265
P.X. Wang, F.Q. Bai, Z.X. Zhang, et al., Org. Electron. 45(2017) 33–41.
doi: 10.1016/j.orgel.2017.02.031
T. Moeller, The Chemistry of the Lanthanides, Pergamon, Great Britain, 1973.
S. Cotton, Lanthanides and Actinides, Macmillan International Higher Education, 1991.
R. Carr, N.H. Evans, D. Parker, Chem. Soc. Rev. 41(2012) 7673–7686.
doi: 10.1039/c2cs35242g
X. Li, W. Liu, Z. Guo, M. Tan, Inorg. Chem. 42(2003) 8735–8738.
doi: 10.1021/ic034268d
B. Wang, Z. Zang, H. Wang, et al., Angew. Chem. 125(2013) 3844–3847.
doi: 10.1002/ange.201210172
Y.H. Sheng, J. Leszczynski, A.A. Garcia, et al., J. Phys. Chem. B 108(2004) 16233–16243.
doi: 10.1021/jp0488867
O. Brugner, T. Reichenbach, M. Sommer, M. Walter, J. Phys. Chem. A 121(2017) 2683–2687.
doi: 10.1021/acs.jpca.7b01248
V.I. Minkin, Chem. Rev. 104(2004) 2751–2776.
doi: 10.1021/cr020088u
L. Cui, H. Zhang, G. Zhang, et al., Spectrochim. Acta A 202(2018) 13–17.
doi: 10.1016/j.saa.2018.04.076
Yi Liu , Zhe-Hao Wang , Guan-Hua Xue , Lin Chen , Li-Hua Yuan , Yi-Wen Li , Da-Gang Yu , Jian-Heng Ye . Photocatalytic dicarboxylation of strained C–C bonds with CO2 via consecutive visible-light-induced electron transfer. Chinese Chemical Letters, 2024, 35(6): 109138-. doi: 10.1016/j.cclet.2023.109138
Pei Cao , Yilan Wang , Lejian Yu , Miao Wang , Liming Zhao , Xu Hou . Dynamic asymmetric mechanical responsive carbon nanotube fiber for ionic logic gate. Chinese Chemical Letters, 2024, 35(6): 109421-. doi: 10.1016/j.cclet.2023.109421
Hang Chen , Chengzhi Cui , Hebo Ye , Hanxun Zou , Lei You . Enhancing hydrolytic stability of dynamic imine bonds and polymers in acidic media with internal protecting groups. Chinese Chemical Letters, 2024, 35(5): 109145-. doi: 10.1016/j.cclet.2023.109145
Tingting Liu , Pengfei Sun , Wei Zhao , Yingshuang Li , Lujun Cheng , Jiahai Fan , Xiaohui Bi , Xiaoping Dong . Magnesium doping to improve the light to heat conversion of OMS-2 for formaldehyde oxidation under visible light irradiation. Chinese Chemical Letters, 2024, 35(4): 108813-. doi: 10.1016/j.cclet.2023.108813
Jianye Kang , Xinyu Yang , Xuhao Yang , Jiahui Sun , Yuhang Liu , Shutao Wang , Wenlong Song . Carbon dots-enhanced pH-responsive lubricating hydrogel based on reversible dynamic covalent bondings. Chinese Chemical Letters, 2024, 35(5): 109297-. doi: 10.1016/j.cclet.2023.109297
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Tian-Yu Gao , Xiao-Yan Mo , Shu-Rong Zhang , Yuan-Xu Jiang , Shu-Ping Luo , Jian-Heng Ye , Da-Gang Yu . Visible-light photoredox-catalyzed carboxylation of aryl epoxides with CO2. Chinese Chemical Letters, 2024, 35(7): 109364-. doi: 10.1016/j.cclet.2023.109364
Lang Gao , Cen Zhou , Rui Wang , Feng Lan , Bohang An , Xiaozhou Huang , Xiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832
Jing Wang , Zenghui Li , Xiaoyang Liu , Bochao Su , Honghong Gong , Chao Feng , Guoping Li , Gang He , Bin Rao . Fine-tuning redox ability of arylene-bridged bis(benzimidazolium) for electrochromism and visible-light photocatalysis. Chinese Chemical Letters, 2024, 35(9): 109473-. doi: 10.1016/j.cclet.2023.109473
Rui Wang , He Qi , Haijiao Zheng , Qiong Jia . Light/pH dual-responsive magnetic metal-organic frameworks composites for phosphorylated peptide enrichment. Chinese Chemical Letters, 2024, 35(7): 109215-. doi: 10.1016/j.cclet.2023.109215
Pingping Wang , Huixian Miao , Kechuan Sheng , Bin Wang , Fan Feng , Xuankun Cai , Wei Huang , Dayu Wu . Efficient blue-light-excitable copper(Ⅰ) coordination network phosphors for high-performance white LEDs. Chinese Chemical Letters, 2024, 35(4): 108600-. doi: 10.1016/j.cclet.2023.108600
Yiyue Ding , Qiuxiang Zhang , Lei Zhang , Qilu Yao , Gang Feng , Zhang-Hui Lu . Exceptional activity of amino-modified rGO-immobilized PdAu nanoclusters for visible light-promoted dehydrogenation of formic acid. Chinese Chemical Letters, 2024, 35(7): 109593-. doi: 10.1016/j.cclet.2024.109593
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