富勒烯硫化反应进展
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摘要
富勒烯官能化研究是富勒烯化学的重要组成部分。近年来,随着富勒烯化学研究的深入发展,许多新颖富勒烯衍生物被陆续合成出来,并在生物医学和有机太阳能电池方面显示出良好的应用潜力。与快速发展的富勒烯化学相比,富勒烯硫化反应研究进展较慢,近年来逐步引起广泛兴趣。在此,我们结合本课题组开展的工作,对富勒烯硫化反应的最新进展进行总结。
Functionalization of fullerenes is an important part of fullerene chemistry. Many novel fullerene derivatives have been synthesized during recent years,and the compounds have exhibited promising potentials in biomedical chemistry and organic solar cells. Compared with the rapid development of fullerene chemistry,progress on the fullerene thiolation is slow,which has attracted more attention recently. Herein,the latest progress on the thiolation reactions of fullerenes is reviewed,which includes the recent result from our group.
Functionalization of fullerenes is an important part of fullerene chemistry. Many novel fullerene derivatives have been synthesized during recent years,and the compounds have exhibited promising potentials in biomedical chemistry and organic solar cells. Compared with the rapid development of fullerene chemistry,progress on the fullerene thiolation is slow,which has attracted more attention recently. Herein,the latest progress on the thiolation reactions of fullerenes is reviewed,which includes the recent result from our group.
引文
[1]Echegoyen L,Echegoyen L E.Electrochemistry of Fullerenes and Their Derivatives[J].Acc Chem Res,1998,31(9):593-601.
[2]Aguirre J C,Arntsen C,Hernandez S,et al.Understanding Local and Macroscopic Electron Mobilities in the Fullerene Network of Conjugated Polymer-Based Solar Cells:Time-Resolved Microwave Conductivity and Theory[J].Adv Funct Mater,2014,24(6):784-792.
[3]Liu T,Troisi A.What Makes Fullerene Acceptors Special as Electron Acceptors in Organic Solar Cells and How to Replace Them[J].Adv Mater,2013,25(7):1038-1041.
[4]Nakanishi I,Fukuzumi S,Konishi T,et al.DNA Cleavage via Superoxide Anion Formed in Photoinduced Electron Transfer from NADH toγ-Cyclodextrin-Bicapped C60in an Oxygen-Saturated Aqueous Solution[J].J Phys Chem B,2002,106(9):2372-2380.
[5]Yamakoshi Y,Umezawa N,Ryu A,et al.Active Oxygen Species Generated from Photoexcited Fullerene(C60)as Potential Medicines:O·-2versus1O2[J].J Am Chem Soc,2003,125(42):12803-12809.
[6]Markovic Z,Trajkovic V.Biomedical Potential of the Reactive Oxygen Species Generation and Quenching by Fullerenes(C60)[J].Biomaterials,2008,29(26):3561-3573.
[7]Wang I C,Tai L A,Lee D D,et al.C60and Water-Soluble Fullerene Derivatives as Antioxidants Against Radical-Initiated Lipid Peroxidation[J].J Med Chem,1999,42(22):4614-4620.
[8]Yin J J,Lao F,Fu P P,et al.The Scavenging of Reactive Oxygen Species and the Potential for Cell Protection by Functionalized Fullerene Materials[J].Biomaterials,2009,30(4):611-621.
[9]Tzirakis M D,Orfanopoulos M.Radical Reactions of Fullerenes:From Synthetic Organic Chemistry to Materials Science and Biology[J].Chem Rev,2013,113(7):5262-5321.
[10]Dennler G,Scharber M C,Brabec C J.Polymer-Fullerene Bulk-Heterojunction Solar Cells[J].Adv Mater,2009,21(13):1323-1338.
[11]Matsuo Y.Design Concept for High-LUMO-Level Fullerene Electron-Acceptors for Organic Solar Cells[J].Chem Lett,2012,41(51):754-759.
[12]Li C Z,Yip H L,Jen A K Y.Functional Fullerenes for Organic Photovoltaics[J].J Mater Chem,2012,22(10):4161-4177.
[13]Li Y.Fullerene-Bisadduct Acceptors for Polymer Solar Cells[J].Chem Asian J,2013,8(10):2316-2328.
[14]Nakamura E,Isobe H.Functionalized Fullerenes in Water.The First 10 Years of Their Chemistry,Biology,and Nanoscience[J].Acc Chem Res,2003,36(11):807-815.
[15]Bosi S,Da Ros T,Spalluto G,et al.Fullerene Derivatives:An Attractive Tool for Biological Applications[J].Eur J Med Chem,2003,38(11/12):913-923.
[16]Bakry R,Vallant R M,Najamul H M,et al.Medicinal Applications of Fullerenes[J].Int J Nanomed,2007,2(4):639-649.
[17]Ra2ovic'I.Water-Soluble Fullerenes for Medical Applications[J].Mater Sci Technol,2017,33(7):777-794.
[18]Castro E,Garcia A H,Zavala G,et al.Fullerenes in Biology and Medicine[J].J Mater Chem B,2017,5(32):6523-6535.
[19]Zhou Y,Li J,Ma H,et al.Biocompatible[60]/[70]Fullerenols:Potent Defense Against Oxidative Injury Induced by Reduplicative Chemotherapy[J].ACS Appl Mater Interfaces,2017,9(41):35539-35547.
[20]Hirsch A,Brettreich M.Fullerenes:Chemistry and Reactions[M].Wiley-VCH Verlag Gmb H&Co.KGa A:Weinheim,Germany:2005.
[21]Yamada M,Akasaka T,Nagase S.Carbene Additions to Fullerenes[J].Chem Rev,2013,113(9):7209-7264.
[22]Matsuo Y,Nakamura E.Selective Multiaddition of Organocopper Reagents to Fullerenes[J].Chem Rev,2008,108(8):3016-3028.
[23]Lu X,Bao L P,Akasaka T,et al.Recent Progress in the Chemistry of Endohedral Metallofullerenes[J].Chem Commun,2014,50(94):14701-14715.
[24]Tzirakis M D,Orfanopoulos M.Radical Reactions of Fullerenes:From Synthetic Organic Chemistry to Materials Science and Biology[J].Chem Rev,2013,113(7):5262-5321.
[25]Martín N.New Challenges in Fullerene Chemistry[J].Chem Commun,2006,37(20):2093-2104.
[26]Thilgen C,Diederich F.Structural Aspects of Fullerene Chemistry-A Journey Through Fullerene Chirality[J].Chem Rev,2006,106(12):5049-5135.
[27]Ohno M,Kojima S,Eguch S.Dihydrothiopyran-fused[60]Fullerene from Hetero-Diels-Alder Reaction with Thioacrylamide and Acyl Chloride[J].J Chem Soc,Chem Commun,1995:565-566.
[28]Ohno M,Kojima S,Shirakawa Y,et al.Hetero-Diels-Alder Reaction of Fullerene:Synthesis of Thiochroman-Fused C60with o-Thioquinone Methide and Oxidation to Its S-Oxides[J].Tetrahedron Lett,1995,36(38):6899-6902.
[29]Duczek W,Tittelbach F,Costisella B,et al.Reaction of[60]Fullerene with 5-Imino-1,2,4-thiadiazolidine-3-ones:Formation of New C60-Fused Heterocycles[J].Tetrahedron,1996,52(26):8733-8738.
[30]Takaguchi Y,Katayose Y,Yanagimoto Y,et al.Photoinduced Dithiolation of Fullerene[60]with Dendrimer Disulfide[J].Chem Lett,2003,32(12):1124-1125.
[31]Izquierdo M,Osuna S,Filippone S,et al.On the Regioselective Intramolecular Nucleophilic Addition of Thiols to C60[J].Eur J Org Chem,2009:6231-6238.
[32]Yang X,Huang S,Jia Z,et al.Reactivity of Fullerene Epoxide:Preparation of Fullerene-Fused Thiirane,Tetrahydrothiazolidin-2-one,and 1,3-Dioxolane[J].J Org Chem,2008,73(7):2518-2526.
[33]Yang X,Gan L,Wang Z.Controlled Regio-and Chemoselective Addition of Isothiocyanate to the Dione Moiety of a Cage-Opened Fullerene-Mixed Peroxide Derivative[J].Chem Commun,2008:1980-1982.
[34]Li F B,Zhu Y F,Zhang X F,et al.Synthesis of Oxazolidinofullerenes/Thiazolidinofullerenes:Novel Reaction of[60]Fullerene with Isocyanates/Isothiocyanates Promoted by Ferric Perchlorate[J].RSC Adv,2014,4(89):48085-48094.
[35]Wang G W,Li J X,Li Y J,et al.Novel Reactions of[60]Fullerene with Amino Acid Esters and Carbon Disulfide[J].JOrg Chem,2006,71(2):680-684.
[36]Li J X,Wang G W.Synthesis of[60]Fullerene-Fused Thiolactams and Thiaimidates[J].Tetrahedron Lett,2012,53(13):1610-1612.
[37]Wu S L,Gao X.Copper-Catalyzed Aerobic Oxidative Reaction of C60with Aliphatic Primary Amines and CS2[J].J Org Chem,2018,83(4):2125-2130.
[38]Isobe H,Tanaka T,Nakanishi W,et al.Regioselective Oxygenative Tetraamination of[60]Fullerene.Fullerene-Mediated Reduction of Molecular Oxygen by Amine via Ground State Single Electron Transfer in Dimethyl Sulfoxide[J].J Org Chem,2005,70(12):4826-4832.
[39]Futagoishi T,Murata M,Wakamiya A,et al.Expansion of Orifices of Open C60Derivatives and Formation of an Open C59SDerivative by Reaction with Sulfur[J].Org Lett,2013,15(11):2750-2753.
[40]Zhang R,Futagoishi T,Murata M,et al.Synthesis and Structure of an Open-Cage Thiafullerene C69S:Reactivity Differences of an Open-Cage C70Tetraketone Relative to Its C60Analogue[J].J Am Chem Soc,2014,136(23):8193-8196.
[41]Khakina E A,Yurkova A A,Peregudov A S,et al.Highly Selective Reactions of C60Cl6with Thiols for the Synthesis of Functionalized[60]Fullerene Derivatives[J].Chem Commun,2012,48(57):7158-7160.
[42]Khakina E A,Peregudov A S,Yurkova A A,et al.Unusual Multistep Reaction of C70Cl10with Thiols Producing C70[SR]5H[J].Tetrahedron Lett,2016,57(11):1215-1219.
[2]Aguirre J C,Arntsen C,Hernandez S,et al.Understanding Local and Macroscopic Electron Mobilities in the Fullerene Network of Conjugated Polymer-Based Solar Cells:Time-Resolved Microwave Conductivity and Theory[J].Adv Funct Mater,2014,24(6):784-792.
[3]Liu T,Troisi A.What Makes Fullerene Acceptors Special as Electron Acceptors in Organic Solar Cells and How to Replace Them[J].Adv Mater,2013,25(7):1038-1041.
[4]Nakanishi I,Fukuzumi S,Konishi T,et al.DNA Cleavage via Superoxide Anion Formed in Photoinduced Electron Transfer from NADH toγ-Cyclodextrin-Bicapped C60in an Oxygen-Saturated Aqueous Solution[J].J Phys Chem B,2002,106(9):2372-2380.
[5]Yamakoshi Y,Umezawa N,Ryu A,et al.Active Oxygen Species Generated from Photoexcited Fullerene(C60)as Potential Medicines:O·-2versus1O2[J].J Am Chem Soc,2003,125(42):12803-12809.
[6]Markovic Z,Trajkovic V.Biomedical Potential of the Reactive Oxygen Species Generation and Quenching by Fullerenes(C60)[J].Biomaterials,2008,29(26):3561-3573.
[7]Wang I C,Tai L A,Lee D D,et al.C60and Water-Soluble Fullerene Derivatives as Antioxidants Against Radical-Initiated Lipid Peroxidation[J].J Med Chem,1999,42(22):4614-4620.
[8]Yin J J,Lao F,Fu P P,et al.The Scavenging of Reactive Oxygen Species and the Potential for Cell Protection by Functionalized Fullerene Materials[J].Biomaterials,2009,30(4):611-621.
[9]Tzirakis M D,Orfanopoulos M.Radical Reactions of Fullerenes:From Synthetic Organic Chemistry to Materials Science and Biology[J].Chem Rev,2013,113(7):5262-5321.
[10]Dennler G,Scharber M C,Brabec C J.Polymer-Fullerene Bulk-Heterojunction Solar Cells[J].Adv Mater,2009,21(13):1323-1338.
[11]Matsuo Y.Design Concept for High-LUMO-Level Fullerene Electron-Acceptors for Organic Solar Cells[J].Chem Lett,2012,41(51):754-759.
[12]Li C Z,Yip H L,Jen A K Y.Functional Fullerenes for Organic Photovoltaics[J].J Mater Chem,2012,22(10):4161-4177.
[13]Li Y.Fullerene-Bisadduct Acceptors for Polymer Solar Cells[J].Chem Asian J,2013,8(10):2316-2328.
[14]Nakamura E,Isobe H.Functionalized Fullerenes in Water.The First 10 Years of Their Chemistry,Biology,and Nanoscience[J].Acc Chem Res,2003,36(11):807-815.
[15]Bosi S,Da Ros T,Spalluto G,et al.Fullerene Derivatives:An Attractive Tool for Biological Applications[J].Eur J Med Chem,2003,38(11/12):913-923.
[16]Bakry R,Vallant R M,Najamul H M,et al.Medicinal Applications of Fullerenes[J].Int J Nanomed,2007,2(4):639-649.
[17]Ra2ovic'I.Water-Soluble Fullerenes for Medical Applications[J].Mater Sci Technol,2017,33(7):777-794.
[18]Castro E,Garcia A H,Zavala G,et al.Fullerenes in Biology and Medicine[J].J Mater Chem B,2017,5(32):6523-6535.
[19]Zhou Y,Li J,Ma H,et al.Biocompatible[60]/[70]Fullerenols:Potent Defense Against Oxidative Injury Induced by Reduplicative Chemotherapy[J].ACS Appl Mater Interfaces,2017,9(41):35539-35547.
[20]Hirsch A,Brettreich M.Fullerenes:Chemistry and Reactions[M].Wiley-VCH Verlag Gmb H&Co.KGa A:Weinheim,Germany:2005.
[21]Yamada M,Akasaka T,Nagase S.Carbene Additions to Fullerenes[J].Chem Rev,2013,113(9):7209-7264.
[22]Matsuo Y,Nakamura E.Selective Multiaddition of Organocopper Reagents to Fullerenes[J].Chem Rev,2008,108(8):3016-3028.
[23]Lu X,Bao L P,Akasaka T,et al.Recent Progress in the Chemistry of Endohedral Metallofullerenes[J].Chem Commun,2014,50(94):14701-14715.
[24]Tzirakis M D,Orfanopoulos M.Radical Reactions of Fullerenes:From Synthetic Organic Chemistry to Materials Science and Biology[J].Chem Rev,2013,113(7):5262-5321.
[25]Martín N.New Challenges in Fullerene Chemistry[J].Chem Commun,2006,37(20):2093-2104.
[26]Thilgen C,Diederich F.Structural Aspects of Fullerene Chemistry-A Journey Through Fullerene Chirality[J].Chem Rev,2006,106(12):5049-5135.
[27]Ohno M,Kojima S,Eguch S.Dihydrothiopyran-fused[60]Fullerene from Hetero-Diels-Alder Reaction with Thioacrylamide and Acyl Chloride[J].J Chem Soc,Chem Commun,1995:565-566.
[28]Ohno M,Kojima S,Shirakawa Y,et al.Hetero-Diels-Alder Reaction of Fullerene:Synthesis of Thiochroman-Fused C60with o-Thioquinone Methide and Oxidation to Its S-Oxides[J].Tetrahedron Lett,1995,36(38):6899-6902.
[29]Duczek W,Tittelbach F,Costisella B,et al.Reaction of[60]Fullerene with 5-Imino-1,2,4-thiadiazolidine-3-ones:Formation of New C60-Fused Heterocycles[J].Tetrahedron,1996,52(26):8733-8738.
[30]Takaguchi Y,Katayose Y,Yanagimoto Y,et al.Photoinduced Dithiolation of Fullerene[60]with Dendrimer Disulfide[J].Chem Lett,2003,32(12):1124-1125.
[31]Izquierdo M,Osuna S,Filippone S,et al.On the Regioselective Intramolecular Nucleophilic Addition of Thiols to C60[J].Eur J Org Chem,2009:6231-6238.
[32]Yang X,Huang S,Jia Z,et al.Reactivity of Fullerene Epoxide:Preparation of Fullerene-Fused Thiirane,Tetrahydrothiazolidin-2-one,and 1,3-Dioxolane[J].J Org Chem,2008,73(7):2518-2526.
[33]Yang X,Gan L,Wang Z.Controlled Regio-and Chemoselective Addition of Isothiocyanate to the Dione Moiety of a Cage-Opened Fullerene-Mixed Peroxide Derivative[J].Chem Commun,2008:1980-1982.
[34]Li F B,Zhu Y F,Zhang X F,et al.Synthesis of Oxazolidinofullerenes/Thiazolidinofullerenes:Novel Reaction of[60]Fullerene with Isocyanates/Isothiocyanates Promoted by Ferric Perchlorate[J].RSC Adv,2014,4(89):48085-48094.
[35]Wang G W,Li J X,Li Y J,et al.Novel Reactions of[60]Fullerene with Amino Acid Esters and Carbon Disulfide[J].JOrg Chem,2006,71(2):680-684.
[36]Li J X,Wang G W.Synthesis of[60]Fullerene-Fused Thiolactams and Thiaimidates[J].Tetrahedron Lett,2012,53(13):1610-1612.
[37]Wu S L,Gao X.Copper-Catalyzed Aerobic Oxidative Reaction of C60with Aliphatic Primary Amines and CS2[J].J Org Chem,2018,83(4):2125-2130.
[38]Isobe H,Tanaka T,Nakanishi W,et al.Regioselective Oxygenative Tetraamination of[60]Fullerene.Fullerene-Mediated Reduction of Molecular Oxygen by Amine via Ground State Single Electron Transfer in Dimethyl Sulfoxide[J].J Org Chem,2005,70(12):4826-4832.
[39]Futagoishi T,Murata M,Wakamiya A,et al.Expansion of Orifices of Open C60Derivatives and Formation of an Open C59SDerivative by Reaction with Sulfur[J].Org Lett,2013,15(11):2750-2753.
[40]Zhang R,Futagoishi T,Murata M,et al.Synthesis and Structure of an Open-Cage Thiafullerene C69S:Reactivity Differences of an Open-Cage C70Tetraketone Relative to Its C60Analogue[J].J Am Chem Soc,2014,136(23):8193-8196.
[41]Khakina E A,Yurkova A A,Peregudov A S,et al.Highly Selective Reactions of C60Cl6with Thiols for the Synthesis of Functionalized[60]Fullerene Derivatives[J].Chem Commun,2012,48(57):7158-7160.
[42]Khakina E A,Peregudov A S,Yurkova A A,et al.Unusual Multistep Reaction of C70Cl10with Thiols Producing C70[SR]5H[J].Tetrahedron Lett,2016,57(11):1215-1219.