噻咯及其衍生物的合成及性能研究进展
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摘要
综述了噻咯、二噻吩并噻咯和含噻咯单元聚合物的合成方法、性能及应用研究进展。
This article reviewed the research progress in the synthesis and applications of silole and its derivatives,including dithienosilole and silole-containing polymers.
This article reviewed the research progress in the synthesis and applications of silole and its derivatives,including dithienosilole and silole-containing polymers.
引文
[1] CHEN J W,CAO Y. Fluorescence responses of 1-methyl-1,2,3,4,5-pentaphenylsilole thin layer to vapors of common solvents[J]. Sens Actuators B,2006,114(1):65-70.
[2] YOO S, DOMERCQ B, KIPPELEN B. Efficient thin-film organic solar cells based on pentacene/C60heterojunctions[J]. Appl Phys Lett,2004,85(22):5427-5429.
[3] MA Z X,BARTON T. Design and synthesis of novel blue-light-emitting photoluminescent monomers and polymers[J]. Polym Prepr,1997,38(2):249-250.
[4] YAMAGUCHI S,XU C H,TAMAO K. Bis-siliconbridged stilbene homologues synthesized by new intramolecular reductive double cyclization[J]. J Am Chem Soc,2003,125(45):13662-13663.
[5] FURUKAWA S,KOBAYASHI J,KAWASHIMA T. Development of a sila-friedel-crafts reaction and its application to the synthesis of dibenzosilole derivatives[J]. J Am Chem Soc,2009,131(40):14192-14193.
[6] FURUKAWA S,KOBAYASHI J,KAWASHIMA T.Application of the sila-friedel-crafts reaction to the synthesis ofπ-extended silole derivatives and their properties[J]. Dalton Trans,2010(39):9329-9336.
[7] OUYANG K,LIANG Y,XI Z F. Construction of benzosiloles, six and eight-membered silacyclic skeletons,via a Pd-catalyzed intramolecular Mizoroki-Heck reaction of vinylsilanes[J]. Organ Lett,2012,14(17):4572-4575.
[8] CURLESS L D,INGLESON M J. B(C6F5)3-catalyzed synthesisofbenzofused-siloles[J].Organometallics,2014,33(24):7241-7246.
[9] ZHANG Q W,AN K,LIU L C,et al. Rhodium-catalyzed intramolecular C—H silylation by silacyclobutanes[J].Angew Chem Int edit,2016,55(21):6319-6323.
[10] ZHAO Z J,LIU D D,LIU P,et al. Theoretical study of substituent effect on the charge mobility of 2,5-bis(trialkylsilylethynyl)-1,1,3,4-tetraphenylsiloles[J]. Sci China Chem,2010,53(11):2311-2317.
[11] ZHAO Z J, LIU D D, MAHTAB F, et al.Synthesis,structure,aggregation-induced emission,self-assembly and electron mobility of 2,5-bis(triphenylsilylethynyl)-3,4-diphenylsiloles[J].Chem Eur J,2011,17(21):5998-6008.
[12] CHEN L,JIANG Y,NIE H,et al. Creation of bifunctional materials:improve electron-transporting ability of light emitters based on aie-active 2,3,4,5-tetraphenylsiloles[J]. Adv Funct Mater,2014,24(23):3621-3630.
[13] YUAN S,WANG L J,HUANG C B,et al. Azasilicon-bridged heterocyclic arylamines:syntheses,structures and photophysical properties[J]. New J Chem,2018,42(4):3102-3111.
[14] XU B W,ZHENG Z,ZHAO K,et al. A bifunctional interlayer material for modifying both the anode and cathode in highly efficient polymer solar cells[J]. Adv Mater,2015,28(3):434-439.
[15] LIN Y,ZHAO F,YANG W,et al. Mapping polymer donors toward high-efficiency fullerene free organic solar cells[J]. Adv Mater,2016,29(3):334-337.
[16] JIA T,ZHOU W,LI F,et al. Alcohol/water-soluble porphyrins as cathode interlayers in high-performance polymer solar cells[J]. Sci China Chem,2015,58(2):323-330.
[17] LIU W,LI S,HUANG J,et al. Nonfullerenetandem organic solar cells with high open-circuit voltage of1. 97V[J]. Adv Mater,2016,28(44):9729-9734.
[18] OHSHITA J. Conjugated oligomers and polymers containing dithienosilole units[J]. Macromol Chem Phys,2009,210(17):1360-1370.
[19] OHSHITA J,NAKASHIMA M,TANAKA D,et al.Preparation of a D-A polymer with disilanobithiophene as a new donor component and application to high-voltage bulk heterojunction polymer solar cells[J]. Polym Chem,2013,5(2):346-349.
[20] OHSHITA J,NODONO M,KAI H,et al. Synthesis and optical,electrochemical,and electron-transporting properties of silicon-bridged bithiophenes[J]. Organometallics,1999,18(8):1453-1459.
[21] OHSHITA J,NODONO M,KAI H,et al. Effects of conjugated substituents on the optical,electrochemical,and electron-transporting properties of dithienosiloles[J]. Organometallics,2001,20(23):4800-4805.
[22] OHSHITA J,NODONO M,WATANABE T,et al.Synthesis and properties of dithienosiloles[J]. Organomet Chem,1998,553(1-2):487-491.
[23] OHSHITA,J,LEE K,KIMURA K,et al. Synthesis of siloles condensed with benzothiophene and indole rings[J]. Organometallics, 2004, 23(23):5622-5625.
[24] TAMAO K,UCHIDA M,IZUMIZAWA T,et al.Silole derivatives as efficient electron transporting materials[J]. J Am Chem Soc, 1996, 118(47):11974-11975.
[25] WU S,HAO L,LIAO Y,et al. Theoretical study on electronic structure and photophysical properties of low band gap dithiophene copolymer with different bridging atoms[J]. Chem Chin Univ Chin,2011,32(4):920-926.
[26] OHSHITA J,TOMINAGA Y,TANAKA D,et al. Synthesis of dithienosilole-based highly photoluminescent donor-acceptor type compounds[J]. Dalton Trans,2013,42(10):3646-3652.
[27] LIU J,SUN X,LI Z F,et al. New D-pi-A system dye based on dithienosilole and carbazole:Synthesis,photo-electrochemical properties and dye-sensitized solar cell performance[J]. J Photochem Photobiol A,2014,294:54-61.
[28] PAPUCCI C,GEERVLIET T A,FRANCHI D,et al.Green/yellow emitting conjugated heterocyclic fluorophores for luminescent solar concentrators[J]. Eur J Org Chem,2018,2018(20-21):2657-2666.
[29] TSUMURA A,KOEZUKA H,ANDO T. Macromolecular electronic device:filed-effect transistor with a polythiophene thin film[J]. Appl Phys Lett,1986,49:1210-1212.
[30] SHERAW C D,ZHOU L,HUANG J R,et al.Organic thin-film transistor-driven polymer-dispersed liquid crystal displays on flexible polymeric substrates[J]. Appl Phys Lett,2002,80(6):1088-1090.
[31] WANG Y,HOU L T,YANG K X,et al. Conjugated silole and carbazole copolymers:synthesis,characterization, single-layer light-emitting diode, and field effect carrier mobility[J]. Macromol Chem Phys,2005,206(21):2190-2198.
[32] USTA H,LU G,FACCHETTI A,et al. Dithienosilole and dibenzosilole-thiophene copolymers as semiconductors for organic thin-film transistors[J]. J Am Chem Soc,2006,128(28):9034-9035.
[33] LU G,USTA H,RISKO C,et al. Synthesis,characterization,and transistor response of semiconducting silole polymers with substantial hole mobility and air stability. experiment and theory[J]. J Am Chem Soc,2008,130(24):7670-7685.
[34] ANDERSEN T R,LARSEN-OLSEN T T,ANDREASEN B,et al. Aqueous processing of low-band-gap polymer solar cells using roll-to-roll methods[J]. ACS Nano,2011,5(5):4188-4196.
[35] TONG M H,CHO S,ROGERS J T,et al. Higher molecular weight leads to improved photoresponsivity,charge transport and interfacial ordering in a narrow bandgap semiconducting polymer[J]. Adv Funct Mater,2010,20(22):3959-3965.
[36] PARK Y D,PARK J K,SEO J H,et al. Solubility-controlled structural ordering of narrow bandgap conjugated polymers[J]. Adv Energy Mater,2011,1(1):63-67.
[37] LI G W,KANG C,GONG X,et al. 5-Alkyloxy-6-fluorobenzo[c][1,2,5]thiadiazole and silafluorene-based d-a alternating conjugated polymers:synthesis and application in polymer photovoltaic cells[J]. Macromolecules,2014,47(14):4645-4652.
[38] HOU J H, CHEN H Y, ZHANG SQ, et al.Synthesis,characterization,and photovoltaic properties of a low band gap polymer based on silole-containing polythiophenes and 2,1,3-benzothiadiazole[J]. J Am Chem Soc,2008,130(48):16144-16145.
[39] WANG E G,WANG L,LAN L F,et al. Highperformance polymer heterojunction solar cells of a polysilafluorene derivative[J]. Appl Phys Lett,2008,92(3):033307-033309.
[40] CAI W Z,WANG M,ZHANG J,et al. Solvent effect leading to high performance of bulk heterojunction polymer solar cells by novel polysilafluorene derivatives[J]. J Phys Chem C,2011,115(5):2314-2319.
[41] LIU L J,SONG J S,LU H,et al. Novel dithienosilole-based conjugated copolymers and its application in bulk heterojunction solar cells[J]. Polym Chem,2016,7(2):319-329.
[42] KIM K,JEON J,HA Y H,et al. Ambipolar charge transport of diketopyrrolepyrrole-silolebased copolymers and effect of side chain engineering:compact model parameter extraction strategy for high-voltage logic applications[J]. Org Electron,2018,54:1-8.
[2] YOO S, DOMERCQ B, KIPPELEN B. Efficient thin-film organic solar cells based on pentacene/C60heterojunctions[J]. Appl Phys Lett,2004,85(22):5427-5429.
[3] MA Z X,BARTON T. Design and synthesis of novel blue-light-emitting photoluminescent monomers and polymers[J]. Polym Prepr,1997,38(2):249-250.
[4] YAMAGUCHI S,XU C H,TAMAO K. Bis-siliconbridged stilbene homologues synthesized by new intramolecular reductive double cyclization[J]. J Am Chem Soc,2003,125(45):13662-13663.
[5] FURUKAWA S,KOBAYASHI J,KAWASHIMA T. Development of a sila-friedel-crafts reaction and its application to the synthesis of dibenzosilole derivatives[J]. J Am Chem Soc,2009,131(40):14192-14193.
[6] FURUKAWA S,KOBAYASHI J,KAWASHIMA T.Application of the sila-friedel-crafts reaction to the synthesis ofπ-extended silole derivatives and their properties[J]. Dalton Trans,2010(39):9329-9336.
[7] OUYANG K,LIANG Y,XI Z F. Construction of benzosiloles, six and eight-membered silacyclic skeletons,via a Pd-catalyzed intramolecular Mizoroki-Heck reaction of vinylsilanes[J]. Organ Lett,2012,14(17):4572-4575.
[8] CURLESS L D,INGLESON M J. B(C6F5)3-catalyzed synthesisofbenzofused-siloles[J].Organometallics,2014,33(24):7241-7246.
[9] ZHANG Q W,AN K,LIU L C,et al. Rhodium-catalyzed intramolecular C—H silylation by silacyclobutanes[J].Angew Chem Int edit,2016,55(21):6319-6323.
[10] ZHAO Z J,LIU D D,LIU P,et al. Theoretical study of substituent effect on the charge mobility of 2,5-bis(trialkylsilylethynyl)-1,1,3,4-tetraphenylsiloles[J]. Sci China Chem,2010,53(11):2311-2317.
[11] ZHAO Z J, LIU D D, MAHTAB F, et al.Synthesis,structure,aggregation-induced emission,self-assembly and electron mobility of 2,5-bis(triphenylsilylethynyl)-3,4-diphenylsiloles[J].Chem Eur J,2011,17(21):5998-6008.
[12] CHEN L,JIANG Y,NIE H,et al. Creation of bifunctional materials:improve electron-transporting ability of light emitters based on aie-active 2,3,4,5-tetraphenylsiloles[J]. Adv Funct Mater,2014,24(23):3621-3630.
[13] YUAN S,WANG L J,HUANG C B,et al. Azasilicon-bridged heterocyclic arylamines:syntheses,structures and photophysical properties[J]. New J Chem,2018,42(4):3102-3111.
[14] XU B W,ZHENG Z,ZHAO K,et al. A bifunctional interlayer material for modifying both the anode and cathode in highly efficient polymer solar cells[J]. Adv Mater,2015,28(3):434-439.
[15] LIN Y,ZHAO F,YANG W,et al. Mapping polymer donors toward high-efficiency fullerene free organic solar cells[J]. Adv Mater,2016,29(3):334-337.
[16] JIA T,ZHOU W,LI F,et al. Alcohol/water-soluble porphyrins as cathode interlayers in high-performance polymer solar cells[J]. Sci China Chem,2015,58(2):323-330.
[17] LIU W,LI S,HUANG J,et al. Nonfullerenetandem organic solar cells with high open-circuit voltage of1. 97V[J]. Adv Mater,2016,28(44):9729-9734.
[18] OHSHITA J. Conjugated oligomers and polymers containing dithienosilole units[J]. Macromol Chem Phys,2009,210(17):1360-1370.
[19] OHSHITA J,NAKASHIMA M,TANAKA D,et al.Preparation of a D-A polymer with disilanobithiophene as a new donor component and application to high-voltage bulk heterojunction polymer solar cells[J]. Polym Chem,2013,5(2):346-349.
[20] OHSHITA J,NODONO M,KAI H,et al. Synthesis and optical,electrochemical,and electron-transporting properties of silicon-bridged bithiophenes[J]. Organometallics,1999,18(8):1453-1459.
[21] OHSHITA J,NODONO M,KAI H,et al. Effects of conjugated substituents on the optical,electrochemical,and electron-transporting properties of dithienosiloles[J]. Organometallics,2001,20(23):4800-4805.
[22] OHSHITA J,NODONO M,WATANABE T,et al.Synthesis and properties of dithienosiloles[J]. Organomet Chem,1998,553(1-2):487-491.
[23] OHSHITA,J,LEE K,KIMURA K,et al. Synthesis of siloles condensed with benzothiophene and indole rings[J]. Organometallics, 2004, 23(23):5622-5625.
[24] TAMAO K,UCHIDA M,IZUMIZAWA T,et al.Silole derivatives as efficient electron transporting materials[J]. J Am Chem Soc, 1996, 118(47):11974-11975.
[25] WU S,HAO L,LIAO Y,et al. Theoretical study on electronic structure and photophysical properties of low band gap dithiophene copolymer with different bridging atoms[J]. Chem Chin Univ Chin,2011,32(4):920-926.
[26] OHSHITA J,TOMINAGA Y,TANAKA D,et al. Synthesis of dithienosilole-based highly photoluminescent donor-acceptor type compounds[J]. Dalton Trans,2013,42(10):3646-3652.
[27] LIU J,SUN X,LI Z F,et al. New D-pi-A system dye based on dithienosilole and carbazole:Synthesis,photo-electrochemical properties and dye-sensitized solar cell performance[J]. J Photochem Photobiol A,2014,294:54-61.
[28] PAPUCCI C,GEERVLIET T A,FRANCHI D,et al.Green/yellow emitting conjugated heterocyclic fluorophores for luminescent solar concentrators[J]. Eur J Org Chem,2018,2018(20-21):2657-2666.
[29] TSUMURA A,KOEZUKA H,ANDO T. Macromolecular electronic device:filed-effect transistor with a polythiophene thin film[J]. Appl Phys Lett,1986,49:1210-1212.
[30] SHERAW C D,ZHOU L,HUANG J R,et al.Organic thin-film transistor-driven polymer-dispersed liquid crystal displays on flexible polymeric substrates[J]. Appl Phys Lett,2002,80(6):1088-1090.
[31] WANG Y,HOU L T,YANG K X,et al. Conjugated silole and carbazole copolymers:synthesis,characterization, single-layer light-emitting diode, and field effect carrier mobility[J]. Macromol Chem Phys,2005,206(21):2190-2198.
[32] USTA H,LU G,FACCHETTI A,et al. Dithienosilole and dibenzosilole-thiophene copolymers as semiconductors for organic thin-film transistors[J]. J Am Chem Soc,2006,128(28):9034-9035.
[33] LU G,USTA H,RISKO C,et al. Synthesis,characterization,and transistor response of semiconducting silole polymers with substantial hole mobility and air stability. experiment and theory[J]. J Am Chem Soc,2008,130(24):7670-7685.
[34] ANDERSEN T R,LARSEN-OLSEN T T,ANDREASEN B,et al. Aqueous processing of low-band-gap polymer solar cells using roll-to-roll methods[J]. ACS Nano,2011,5(5):4188-4196.
[35] TONG M H,CHO S,ROGERS J T,et al. Higher molecular weight leads to improved photoresponsivity,charge transport and interfacial ordering in a narrow bandgap semiconducting polymer[J]. Adv Funct Mater,2010,20(22):3959-3965.
[36] PARK Y D,PARK J K,SEO J H,et al. Solubility-controlled structural ordering of narrow bandgap conjugated polymers[J]. Adv Energy Mater,2011,1(1):63-67.
[37] LI G W,KANG C,GONG X,et al. 5-Alkyloxy-6-fluorobenzo[c][1,2,5]thiadiazole and silafluorene-based d-a alternating conjugated polymers:synthesis and application in polymer photovoltaic cells[J]. Macromolecules,2014,47(14):4645-4652.
[38] HOU J H, CHEN H Y, ZHANG SQ, et al.Synthesis,characterization,and photovoltaic properties of a low band gap polymer based on silole-containing polythiophenes and 2,1,3-benzothiadiazole[J]. J Am Chem Soc,2008,130(48):16144-16145.
[39] WANG E G,WANG L,LAN L F,et al. Highperformance polymer heterojunction solar cells of a polysilafluorene derivative[J]. Appl Phys Lett,2008,92(3):033307-033309.
[40] CAI W Z,WANG M,ZHANG J,et al. Solvent effect leading to high performance of bulk heterojunction polymer solar cells by novel polysilafluorene derivatives[J]. J Phys Chem C,2011,115(5):2314-2319.
[41] LIU L J,SONG J S,LU H,et al. Novel dithienosilole-based conjugated copolymers and its application in bulk heterojunction solar cells[J]. Polym Chem,2016,7(2):319-329.
[42] KIM K,JEON J,HA Y H,et al. Ambipolar charge transport of diketopyrrolepyrrole-silolebased copolymers and effect of side chain engineering:compact model parameter extraction strategy for high-voltage logic applications[J]. Org Electron,2018,54:1-8.