Calixarene/pillararene-based supramolecular selective binding and molecular assembly
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摘要
Calixa re nes and pillararenes are cyclic oligomers containing repeating units of phenol and methane.The modification of ionized groups bring calixarenes and pillararenes derivates both good water solubility and strong binding affinities towards various organic/inorga nic/biological guest molecules in both water and the solid state.Meanwhile,the pre-organized structures of these compounds are indispensable in constructing of stimuli-responsive supramolecular assembly.With these properties,the supramolecular selective binding and molecular assembly based on calixarene/pillararene are widely used in enzyme tandem assay,stimuli-responsive nanostructure,drug delivery,organelle fluorescent imaging,photocontrolled morphological change,organic and inorganic hybrid material,solid tunable photoluminescence and so on.This review summarized the recent research progresses on the calixarene/pillarare ne-based supramolecular systems and discussed the expectation of the future development.
Calixa re nes and pillararenes are cyclic oligomers containing repeating units of phenol and methane.The modification of ionized groups bring calixarenes and pillararenes derivates both good water solubility and strong binding affinities towards various organic/inorga nic/biological guest molecules in both water and the solid state.Meanwhile,the pre-organized structures of these compounds are indispensable in constructing of stimuli-responsive supramolecular assembly.With these properties,the supramolecular selective binding and molecular assembly based on calixarene/pillararene are widely used in enzyme tandem assay,stimuli-responsive nanostructure,drug delivery,organelle fluorescent imaging,photocontrolled morphological change,organic and inorganic hybrid material,solid tunable photoluminescence and so on.This review summarized the recent research progresses on the calixarene/pillarare ne-based supramolecular systems and discussed the expectation of the future development.
Calixa re nes and pillararenes are cyclic oligomers containing repeating units of phenol and methane.The modification of ionized groups bring calixarenes and pillararenes derivates both good water solubility and strong binding affinities towards various organic/inorga nic/biological guest molecules in both water and the solid state.Meanwhile,the pre-organized structures of these compounds are indispensable in constructing of stimuli-responsive supramolecular assembly.With these properties,the supramolecular selective binding and molecular assembly based on calixarene/pillararene are widely used in enzyme tandem assay,stimuli-responsive nanostructure,drug delivery,organelle fluorescent imaging,photocontrolled morphological change,organic and inorganic hybrid material,solid tunable photoluminescence and so on.This review summarized the recent research progresses on the calixarene/pillarare ne-based supramolecular systems and discussed the expectation of the future development.
引文
[1]Y.Wang,H.Xu,X.Zhang,Adv.Mater.21(2009)2849-2864.
[2]W.Pisula,M.Kastler,D.Wasserfallen,et al.,Angew.Chem.Int.Ed.45(2006)819-823.
[3]C.Wang,S.Yin,S.Chen,et al.,Angew.Chem.Int Ed.47(2008)9049-9052.
[4]X.Zhang,S.Rehm,M.M.Safont-Sempere,F.Würthner,Nat.Chem.1(2009)623.
[5]Y.Wang,N.Ma,Z.Wang,X.Zhang,Angew.Chem.Int.Ed.46(2007)2823-2826.
[6]K.Kim,W.S.Jeon,J.K.Kang,et al.,Angew.Chem.Int.Ed.42(2003)2293-2296.
[7]N.Kimizuka,T.Kawasaki,T.Kunitake,J.Am.Chem.Soc.115(1993)4387-4388.
[8]N.Kimizuka,T.Kawasaki,K.Hirata,T.Kunitake,J.Am.Chem.Soc.120(1998)4094-4104.
[9]X.Zhang,Z.Chen,F.Wurthner,J.Am.Chem.Soc.129(2007)4886-4887.
[10]V.Balzani,M.Gómez-López,J.F.Stoddart,Acc.Chem.Res.31(1998)405-414.
[11]M.J.Blanco,M.Consuelo Jiménez,J.C.Chambron,et al.,Chem.Soc.Rev.28(1999)293-305.
[12]J.P.Sauvage,Acc.Chem.Res.31(1998)611-619.
[13]Y.Liu,M.Han,H.Y.Zhang,L.X.Yang,W.Jiang,Org.Lett.10(2008)2873-2876.
[14]M.Suresh,A.K.Mandal,E.Suresh,A.Das,Chem.Sci.4(2013)2380-2386.
[15]H.Xu,D.M.Rudkevich,J.Org.Che.69(2004)8609-8617.
[16]S.Shinkai,S.Mori,T.Tsubaki,T.Sone,O.Manabe,Tetrahedron Lett.25(1984)5315-5318.
[17]S.Shinkai,K.Araki,T.Matsuda,et al.,J.Am.Chem.Soc. 112(1990)9053-9058.
[18]Y.Liu,D.S.Guo,H.Y.Zhang,Y.H.Ma,E.C.Yang,J.Phy.Chem.B 110(2006)3428-3434.
[19]H.X. Zhao,D.S.Guo,Y.Liu,J.Phy.Chem.B 117(2013)1978-1987.
[20]G.S.Wang,H.Y.Zhang,D.Li,P.Y.Wang,Y.Liu,Supramol.Chem.23(2011)441-446.
[21] G.S.Wang,H.Y.Zhang,F.Ding,Y.Liu,J.Inclusion Phenom.Macrocyclic Chem.69(2011)85-89.
[22]D.S.Guo,H.Q.Zhang,F.Ding,Y.Liu,Org.Biomol.Chem.10(2012)1527-1536.
[23]K.Wang,D.S.Guo,H.H.Zhang,et al.,J.Med.Chem.52(2009)6402-6412.
[24]J.M.Hatcher,K.D.Pennell,G.W.Miller,Trends Pharmacol.Sci.29(2008)322-329.
[25]R.J.Dinis-Oliveira,F.Remiao,H.Carmo,et al.,Neurotoxicology 27(2006)1110-1122.
[26]H.Bakirci,W.M.Nau,Adv.Funct.Mater.16(2006)237-242.
[27]T.Jin,Sensors 10(2010)2438-2449.
[28]T.Jin,F.Fujii,Y.Ooi,Sensors 8(2008)6777-6790.
[29]K.N.Koh,K.Araki,A.Ikeda,H.Otsuka,S.Shinkai,J.Am.Chem.Soc.118(1996)755-758.
[30]D.S.Guo,V.D.Uzunova,X.Su,Y.Liu,W.M.Nau,Chem.Sci.2(2011)1722-1734.
[31]Q.Zhao,Y.Chen,S.H.Li,Y.Liu,Chem.Commun.54(2018)200-203.
[32]B.Hua,L. Shao,G.Yu,F.Huang,Chem.Commun.52(2016)10016-10019.
[33]D.S.Guo,K.Chen,H.Q.Zhang,Y.Liu,Chem.-Asian J.4(2009)436-445.
[34]D.S.Guo,B.P.Jiang,X.Wang,Y.Liu,Org.Biomol.Chem.10(2012)720-723.
[35]O.Varga,M.Kubinyi,T.Vidoczy,et al.,J.Photochem.Photobiol.A:Chem.207(2009)167-172.
[36]V.Lau,B.Heyne,Chem.Commun.46(2010)3595-3597.
[37]M.Megyesi,L.Biczok,J.Phy.Chem.B 114(2010)2814-2819.
[38]N.Basilio,A.Pineiro,J.P.Da Silva,L.Garcia-Rio,J.Org.Chem.78(2013)9113-9119.
[39]N.Basilio,L García-Río,Chem.-Eur.J.15(2009)9315-9319.
[40]V.Francisco,N.Basilio,L.Garcia-Rio,et al.,Chem.Commun.46(2010)6551-6553.
[41]N.Basilio,B.Gómez,L.Garcia-Rio,V.Francisco,Chem.-Eur.J.19(2013)4570-4576.
[42]N.Basilio,M.Martin-Pastor,L Garcia-Rio,Langmuir 28(2012)6561-6568.
[43]V.Wintgens,C.Le Coeur,C.Amiel,et al.,Langmuir 29(2013)7682-7688.
[44]K.Wang,D.S.Guo,Y.Liu,Chem.-Eur.J.16(2010)8006-8011.
[45]K.Wang,D.S.Guo,Y.Liu,Chem.-Eur.J.18(2012)8758-8764.
[46]K.Wang,D.S.Guo,X.Wang,Y.Liu,ACS Nano 5(2011)2880-2894.
[47]D.S.Guo,K.Wang,Y.X.Wang,Y.Liu,J.Am.Chem.Soc.134(2012)10244-10250.
[48]Y.X.Wang,D.S.Guo,Y.C.Duan,Y.J.Wang,Y.Liu,Sci.Rep.5(2015)9019.
[49]A.R(o|¨)sler,G.W.M.Vandermeulen,H.A.Klok,Adv.Drug Deliv.Rev.53(2001)95-108.
[50]F.Gu,L.Zhang,B.A.Teply,et al.,Proc.Nat.Acad.Sci.105(2008)2586.
[51]Y.X.Wang,Y.M.Zhang,Y.L.Wang,Y.Liu,Chem.Mater.27(2015)2848-2854.
[52]Y.X.Wang,Y.M.Zhang,Y.Liu,J.Am.Chem.Soc.137(2015)4543-4549.
[53]X.M.Chen,Y.Chen,Q.Yu,B.H.Gu,Y.Liu,Angew.Chem.Inter.Ed.57(2018)12519-12523.
[54]G.Yu,X.Zhou,Z.Zhang,et al.,J.Am.Chem.Soc. 134(2012)19489-19497.
[55]X.Chi,G.Yu,L.Shao,J.Chen,F.Huang,J.Am.Chem.Soc.138(2016)3168-3174.
[56] G.Yu,W.Yu,L.Shao,et al.,Adv.Funct.Mater.26(2016)8999-9008.
[57]K.Jie,Y.Zhou,Y.Yao, B.Shi,F.Huang,J.Am.Chem.Soc.137(2015)10472-10475.
[58]G.Yu,J.Zhou,J.Shen,G.Tang, F.Huang,Chem.Sci.7(2016)4073-4078.
[59]G.Yu,W.Yu,Z.Mao, C.Gao,F. Huang,Small 11(2015)919-925.
[60]X.Chi,X.Ji, D.Xia,F.Huang,J.Am.Chem.Soc. 137(2015)1440-1443.
[61]B.Shi,K.Jie,Y.Zhou,et al.,J.Am.Chem.Soc.138(2016)80-83.
[62]X.Y.Hu,L. Gao,S.Mosel,et al.,Small 14(2018)1803952.
[63]M.Zuo,W.Qian,T.Li, et al.,ACS Appl.Mater.Interfaces 10(2018)39214-39221.
[64]M.Zuo,W.Qian,Z.Xu,et al.,Small 14(2018)1801942.
[65]S.Guo,Y.Song,Y He,X.Y.Hu,L.Wang;Angew.Chem.Inter.Ed.57(2018)3163-3167.
[66] X.Liu,W.Shao,Y.Zheng,et al.,Chem.Commun.53(2017)8596-8599.
[67]X.Liu,K.Jia, Y.Wang,et al., ACS Appl.Mater.Interfaces 9(2017)4843-4850.
[68]J.R.W,,Y.W.Yang,Chem.Commun.55(2019)1533-1543.
[69]T.Xiao,W.Zhong,L.Zhou,et al., Chin.Chem.Lett.30(2019)31-36.
[70]T.Xiao,L Zhou,L. Xu,et al.,Chin.Chem.Lett. 30(2019)271-276.
[71]Y.Zhou,H.Li, Y.W.Yang,Chin.Chem.Lett.26(2015)825-828.
[72]N.Song,T.Kakuta,T.a.Yamagishi,Y.W.Yang,T.Ogoshi,Chemistry 4(2018)2029-2053.
[73]C.C.Zhang,S.H.Li,C.F. Zhang,Y.Liu,Sci.Rep.6(2016)37014.
[74]N.Cheng,Y.Chen,X.Wu,Y.Liu,Chem.Commun.54(2018)6284-6287.
[75]Q.Zhao,Y.Liu,Chem.Commun.54(2018)6068-6071.
[76] Q.Zhao,Y.Liu,Chem.Commun.54(2018)7362-7365.
[2]W.Pisula,M.Kastler,D.Wasserfallen,et al.,Angew.Chem.Int.Ed.45(2006)819-823.
[3]C.Wang,S.Yin,S.Chen,et al.,Angew.Chem.Int Ed.47(2008)9049-9052.
[4]X.Zhang,S.Rehm,M.M.Safont-Sempere,F.Würthner,Nat.Chem.1(2009)623.
[5]Y.Wang,N.Ma,Z.Wang,X.Zhang,Angew.Chem.Int.Ed.46(2007)2823-2826.
[6]K.Kim,W.S.Jeon,J.K.Kang,et al.,Angew.Chem.Int.Ed.42(2003)2293-2296.
[7]N.Kimizuka,T.Kawasaki,T.Kunitake,J.Am.Chem.Soc.115(1993)4387-4388.
[8]N.Kimizuka,T.Kawasaki,K.Hirata,T.Kunitake,J.Am.Chem.Soc.120(1998)4094-4104.
[9]X.Zhang,Z.Chen,F.Wurthner,J.Am.Chem.Soc.129(2007)4886-4887.
[10]V.Balzani,M.Gómez-López,J.F.Stoddart,Acc.Chem.Res.31(1998)405-414.
[11]M.J.Blanco,M.Consuelo Jiménez,J.C.Chambron,et al.,Chem.Soc.Rev.28(1999)293-305.
[12]J.P.Sauvage,Acc.Chem.Res.31(1998)611-619.
[13]Y.Liu,M.Han,H.Y.Zhang,L.X.Yang,W.Jiang,Org.Lett.10(2008)2873-2876.
[14]M.Suresh,A.K.Mandal,E.Suresh,A.Das,Chem.Sci.4(2013)2380-2386.
[15]H.Xu,D.M.Rudkevich,J.Org.Che.69(2004)8609-8617.
[16]S.Shinkai,S.Mori,T.Tsubaki,T.Sone,O.Manabe,Tetrahedron Lett.25(1984)5315-5318.
[17]S.Shinkai,K.Araki,T.Matsuda,et al.,J.Am.Chem.Soc. 112(1990)9053-9058.
[18]Y.Liu,D.S.Guo,H.Y.Zhang,Y.H.Ma,E.C.Yang,J.Phy.Chem.B 110(2006)3428-3434.
[19]H.X. Zhao,D.S.Guo,Y.Liu,J.Phy.Chem.B 117(2013)1978-1987.
[20]G.S.Wang,H.Y.Zhang,D.Li,P.Y.Wang,Y.Liu,Supramol.Chem.23(2011)441-446.
[21] G.S.Wang,H.Y.Zhang,F.Ding,Y.Liu,J.Inclusion Phenom.Macrocyclic Chem.69(2011)85-89.
[22]D.S.Guo,H.Q.Zhang,F.Ding,Y.Liu,Org.Biomol.Chem.10(2012)1527-1536.
[23]K.Wang,D.S.Guo,H.H.Zhang,et al.,J.Med.Chem.52(2009)6402-6412.
[24]J.M.Hatcher,K.D.Pennell,G.W.Miller,Trends Pharmacol.Sci.29(2008)322-329.
[25]R.J.Dinis-Oliveira,F.Remiao,H.Carmo,et al.,Neurotoxicology 27(2006)1110-1122.
[26]H.Bakirci,W.M.Nau,Adv.Funct.Mater.16(2006)237-242.
[27]T.Jin,Sensors 10(2010)2438-2449.
[28]T.Jin,F.Fujii,Y.Ooi,Sensors 8(2008)6777-6790.
[29]K.N.Koh,K.Araki,A.Ikeda,H.Otsuka,S.Shinkai,J.Am.Chem.Soc.118(1996)755-758.
[30]D.S.Guo,V.D.Uzunova,X.Su,Y.Liu,W.M.Nau,Chem.Sci.2(2011)1722-1734.
[31]Q.Zhao,Y.Chen,S.H.Li,Y.Liu,Chem.Commun.54(2018)200-203.
[32]B.Hua,L. Shao,G.Yu,F.Huang,Chem.Commun.52(2016)10016-10019.
[33]D.S.Guo,K.Chen,H.Q.Zhang,Y.Liu,Chem.-Asian J.4(2009)436-445.
[34]D.S.Guo,B.P.Jiang,X.Wang,Y.Liu,Org.Biomol.Chem.10(2012)720-723.
[35]O.Varga,M.Kubinyi,T.Vidoczy,et al.,J.Photochem.Photobiol.A:Chem.207(2009)167-172.
[36]V.Lau,B.Heyne,Chem.Commun.46(2010)3595-3597.
[37]M.Megyesi,L.Biczok,J.Phy.Chem.B 114(2010)2814-2819.
[38]N.Basilio,A.Pineiro,J.P.Da Silva,L.Garcia-Rio,J.Org.Chem.78(2013)9113-9119.
[39]N.Basilio,L García-Río,Chem.-Eur.J.15(2009)9315-9319.
[40]V.Francisco,N.Basilio,L.Garcia-Rio,et al.,Chem.Commun.46(2010)6551-6553.
[41]N.Basilio,B.Gómez,L.Garcia-Rio,V.Francisco,Chem.-Eur.J.19(2013)4570-4576.
[42]N.Basilio,M.Martin-Pastor,L Garcia-Rio,Langmuir 28(2012)6561-6568.
[43]V.Wintgens,C.Le Coeur,C.Amiel,et al.,Langmuir 29(2013)7682-7688.
[44]K.Wang,D.S.Guo,Y.Liu,Chem.-Eur.J.16(2010)8006-8011.
[45]K.Wang,D.S.Guo,Y.Liu,Chem.-Eur.J.18(2012)8758-8764.
[46]K.Wang,D.S.Guo,X.Wang,Y.Liu,ACS Nano 5(2011)2880-2894.
[47]D.S.Guo,K.Wang,Y.X.Wang,Y.Liu,J.Am.Chem.Soc.134(2012)10244-10250.
[48]Y.X.Wang,D.S.Guo,Y.C.Duan,Y.J.Wang,Y.Liu,Sci.Rep.5(2015)9019.
[49]A.R(o|¨)sler,G.W.M.Vandermeulen,H.A.Klok,Adv.Drug Deliv.Rev.53(2001)95-108.
[50]F.Gu,L.Zhang,B.A.Teply,et al.,Proc.Nat.Acad.Sci.105(2008)2586.
[51]Y.X.Wang,Y.M.Zhang,Y.L.Wang,Y.Liu,Chem.Mater.27(2015)2848-2854.
[52]Y.X.Wang,Y.M.Zhang,Y.Liu,J.Am.Chem.Soc.137(2015)4543-4549.
[53]X.M.Chen,Y.Chen,Q.Yu,B.H.Gu,Y.Liu,Angew.Chem.Inter.Ed.57(2018)12519-12523.
[54]G.Yu,X.Zhou,Z.Zhang,et al.,J.Am.Chem.Soc. 134(2012)19489-19497.
[55]X.Chi,G.Yu,L.Shao,J.Chen,F.Huang,J.Am.Chem.Soc.138(2016)3168-3174.
[56] G.Yu,W.Yu,L.Shao,et al.,Adv.Funct.Mater.26(2016)8999-9008.
[57]K.Jie,Y.Zhou,Y.Yao, B.Shi,F.Huang,J.Am.Chem.Soc.137(2015)10472-10475.
[58]G.Yu,J.Zhou,J.Shen,G.Tang, F.Huang,Chem.Sci.7(2016)4073-4078.
[59]G.Yu,W.Yu,Z.Mao, C.Gao,F. Huang,Small 11(2015)919-925.
[60]X.Chi,X.Ji, D.Xia,F.Huang,J.Am.Chem.Soc. 137(2015)1440-1443.
[61]B.Shi,K.Jie,Y.Zhou,et al.,J.Am.Chem.Soc.138(2016)80-83.
[62]X.Y.Hu,L. Gao,S.Mosel,et al.,Small 14(2018)1803952.
[63]M.Zuo,W.Qian,T.Li, et al.,ACS Appl.Mater.Interfaces 10(2018)39214-39221.
[64]M.Zuo,W.Qian,Z.Xu,et al.,Small 14(2018)1801942.
[65]S.Guo,Y.Song,Y He,X.Y.Hu,L.Wang;Angew.Chem.Inter.Ed.57(2018)3163-3167.
[66] X.Liu,W.Shao,Y.Zheng,et al.,Chem.Commun.53(2017)8596-8599.
[67]X.Liu,K.Jia, Y.Wang,et al., ACS Appl.Mater.Interfaces 9(2017)4843-4850.
[68]J.R.W,,Y.W.Yang,Chem.Commun.55(2019)1533-1543.
[69]T.Xiao,W.Zhong,L.Zhou,et al., Chin.Chem.Lett.30(2019)31-36.
[70]T.Xiao,L Zhou,L. Xu,et al.,Chin.Chem.Lett. 30(2019)271-276.
[71]Y.Zhou,H.Li, Y.W.Yang,Chin.Chem.Lett.26(2015)825-828.
[72]N.Song,T.Kakuta,T.a.Yamagishi,Y.W.Yang,T.Ogoshi,Chemistry 4(2018)2029-2053.
[73]C.C.Zhang,S.H.Li,C.F. Zhang,Y.Liu,Sci.Rep.6(2016)37014.
[74]N.Cheng,Y.Chen,X.Wu,Y.Liu,Chem.Commun.54(2018)6284-6287.
[75]Q.Zhao,Y.Liu,Chem.Commun.54(2018)6068-6071.
[76] Q.Zhao,Y.Liu,Chem.Commun.54(2018)7362-7365.