메뉴 건너뛰기




Volumn 118, Issue 4, 2014, Pages 1793-1799

Effect of substituents on optical properties and charge-carrier polarity of squaraine dyes

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE-CARRIER MOBILITY; COPLANARITY; ELECTRON-DONATING; ELECTRONWITHDRAWING; INTRAMOLECULAR CHARGE TRANSFERS; LONG WAVELENGTH; SQUARAINE DYES; TRIARYLAMINES;

EID: 84893314841     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp410362d     Document Type: Article
Times cited : (23)

References (40)
  • 1
    • 66649129011 scopus 로고    scopus 로고
    • Generation of Triarylamine Radical Cations through Reaction of Triarylamines with Cu(II) in Acetonitrile. A Kinetic Investigation of the Electron-Transfer Reaction
    • Sreenath, K.; Suneesh, C. V.; Gopidas, K. R.; Flowers, R. A. Generation of Triarylamine Radical Cations through Reaction of Triarylamines with Cu(II) in Acetonitrile. A Kinetic Investigation of the Electron-Transfer Reaction J. Phys. Chem. A 2009, 113, 6477-6483
    • (2009) J. Phys. Chem. A , vol.113 , pp. 6477-6483
    • Sreenath, K.1    Suneesh, C.V.2    Gopidas, K.R.3    Flowers, R.A.4
  • 2
    • 0042745574 scopus 로고    scopus 로고
    • Intervalence Charge-Transfer Bands in Triphenylamine-Based Polymers
    • Lambert, C.; Nöll, G. Intervalence Charge-Transfer Bands in Triphenylamine-Based Polymers Synth. Met. 2003, 139, 57-62
    • (2003) Synth. Met. , vol.139 , pp. 57-62
    • Lambert, C.1    Nöll, G.2
  • 3
    • 84886861771 scopus 로고    scopus 로고
    • Charge Transfer Through Cross-Hyperconjugated Versus Cross-[Small Pi]-Conjugated Bridges: An Intervalence Charge Transfer Study
    • Goransson, E.; Emanuelsson, R.; Jorner, K.; Markle, T. F.; Hammarstrom, L.; Ottosson, H. Charge Transfer Through Cross-Hyperconjugated Versus Cross-[Small Pi]-Conjugated Bridges: An Intervalence Charge Transfer Study Chem. Sci. 2013, 4, 3522-3532
    • (2013) Chem. Sci. , vol.4 , pp. 3522-3532
    • Goransson, E.1    Emanuelsson, R.2    Jorner, K.3    Markle, T.F.4    Hammarstrom, L.5    Ottosson, H.6
  • 4
    • 70349908045 scopus 로고    scopus 로고
    • A Spiro-Fused Triarylaminium Radical Cation with a Triplet Ground State
    • Ito, A.; Urabe, M.; Tanaka, K. A Spiro-Fused Triarylaminium Radical Cation with a Triplet Ground State Angew. Chem., Int. Ed. 2009, 48, 5785-5785
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 5785-5785
    • Ito, A.1    Urabe, M.2    Tanaka, K.3
  • 5
    • 31444445296 scopus 로고    scopus 로고
    • Room-Temperature High-Spin Organic Single Molecule: Nanometer-Sized and Hyperbranched Poly[1,2,(4)-phenylenevinyleneanisylaminium]
    • Fukuzaki, E.; Nishide, H. Room-Temperature High-Spin Organic Single Molecule: Nanometer-Sized and Hyperbranched Poly[1,2,(4)- phenylenevinyleneanisylaminium] J. Am. Chem. Soc. 2005, 128, 996-1001
    • (2005) J. Am. Chem. Soc. , vol.128 , pp. 996-1001
    • Fukuzaki, E.1    Nishide, H.2
  • 6
    • 0842307446 scopus 로고    scopus 로고
    • A High-Spin and Durable Polyradical: Poly(4-diphenylaminium-1,2- phenylenevinylene)
    • Murata, H.; Takahashi, M.; Namba, K.; Takahashi, N.; Nishide, H. A High-Spin and Durable Polyradical: Poly(4-diphenylaminium-1,2-phenylenevinylene) J. Org. Chem. 2004, 69, 631-638
    • (2004) J. Org. Chem. , vol.69 , pp. 631-638
    • Murata, H.1    Takahashi, M.2    Namba, K.3    Takahashi, N.4    Nishide, H.5
  • 8
    • 0037189701 scopus 로고    scopus 로고
    • Star-Shaped, Dendrimeric and Polymeric Triarylamines as Photoconductors and Hole Transport Materials for Electro-Optical Applications
    • Thelakkat, M. Star-Shaped, Dendrimeric and Polymeric Triarylamines as Photoconductors and Hole Transport Materials for Electro-Optical Applications Macromol. Mater. Eng. 2002, 287, 442-461
    • (2002) Macromol. Mater. Eng. , vol.287 , pp. 442-461
    • Thelakkat, M.1
  • 9
    • 84871926398 scopus 로고    scopus 로고
    • Synthesis and Characterization of Polytriphenylamine Based Graft Polymers for Photorefractive Application
    • Cao, Z.; Abe, Y.; Nagahama, T.; Tsuchiya, K.; Ogino, K. Synthesis and Characterization of Polytriphenylamine Based Graft Polymers for Photorefractive Application Polymer 2013, 54, 269-276
    • (2013) Polymer , vol.54 , pp. 269-276
    • Cao, Z.1    Abe, Y.2    Nagahama, T.3    Tsuchiya, K.4    Ogino, K.5
  • 10
    • 77950225872 scopus 로고    scopus 로고
    • Non-Linear Optical Polymers for Photorefractive Applications
    • Thomas, J.; Norwood, R. A.; Peyghambarian, N. Non-Linear Optical Polymers for Photorefractive Applications J. Mater. Chem. 2009, 19, 7476-7489
    • (2009) J. Mater. Chem. , vol.19 , pp. 7476-7489
    • Thomas, J.1    Norwood, R.A.2    Peyghambarian, N.3
  • 11
    • 0035178852 scopus 로고    scopus 로고
    • Effect of Substitution on the Electrochemical and Xerographic Properties of Triarylamines: Correlation to the Hammett Parameter of the Substituent and Calculated HOMO Energy Level
    • Bender, T. P.; Graham, J. F.; Duff, J. M. Effect of Substitution on the Electrochemical and Xerographic Properties of Triarylamines: Correlation to the Hammett Parameter of the Substituent and Calculated HOMO Energy Level Chem. Mater. 2001, 13, 4105-4111
    • (2001) Chem. Mater. , vol.13 , pp. 4105-4111
    • Bender, T.P.1    Graham, J.F.2    Duff, J.M.3
  • 12
    • 79952136851 scopus 로고    scopus 로고
    • Star-Shaped Oligotriarylamines with Planarized Triphenylamine Core: Solution-Processable, High-Tg Hole-Injecting and Hole-Transporting Materials for Organic Light-Emitting Devices
    • Jiang, Z.; Ye, T.; Yang, C.; Yang, D.; Zhu, M.; Zhong, C.; Qin, J.; Ma, D. Star-Shaped Oligotriarylamines with Planarized Triphenylamine Core: Solution-Processable, High-Tg Hole-Injecting and Hole-Transporting Materials for Organic Light-Emitting Devices Chem. Mater. 2010, 23, 771-777
    • (2010) Chem. Mater. , vol.23 , pp. 771-777
    • Jiang, Z.1    Ye, T.2    Yang, C.3    Yang, D.4    Zhu, M.5    Zhong, C.6    Qin, J.7    Ma, D.8
  • 13
    • 33846376761 scopus 로고    scopus 로고
    • Synthesis and Properties of Multi-Triarylamine-Substituted Carbazole-Based Dendrimers with an Oligothiophene Core for Potential Applications in Organic Solar Cells and Light-Emitting Diodes
    • Lu, J.; Xia, P. F.; Lo, P. K.; Tao, Y.; Wong, M. S. Synthesis and Properties of Multi-Triarylamine-Substituted Carbazole-Based Dendrimers with an Oligothiophene Core for Potential Applications in Organic Solar Cells and Light-Emitting Diodes Chem. Mater. 2006, 18, 6194-6203
    • (2006) Chem. Mater. , vol.18 , pp. 6194-6203
    • Lu, J.1    Xia, P.F.2    Lo, P.K.3    Tao, Y.4    Wong, M.S.5
  • 14
    • 0037383376 scopus 로고    scopus 로고
    • Synthesis and Stability Studies of Conformationally Locked 4-(diarylamino)aryl- and 4-(dialkylamino)phenyl-Substituted Second-Order Nonlinear Optical Polyene Chromophores
    • Staub, K.; Levina, G. A.; Barlow, S.; Kowalczyk, T. C.; Lackritz, H. S.; Barzoukas, M.; Fort, A.; Marder, S. R. Synthesis and Stability Studies of Conformationally Locked 4-(diarylamino)aryl- and 4-(dialkylamino)phenyl- Substituted Second-Order Nonlinear Optical Polyene Chromophores J. Mater. Chem. 2003, 13, 825-833
    • (2003) J. Mater. Chem. , vol.13 , pp. 825-833
    • Staub, K.1    Levina, G.A.2    Barlow, S.3    Kowalczyk, T.C.4    Lackritz, H.S.5    Barzoukas, M.6    Fort, A.7    Marder, S.R.8
  • 15
    • 84867725174 scopus 로고    scopus 로고
    • Improved Nonlinearity-Transparency-Thermal Stability Trade-Off with Spirobifluorene-Bridged Donor-π-Acceptor Chromophores
    • Xiao, H.; Yin, H.; Zhang, X. Improved Nonlinearity-Transparency-Thermal Stability Trade-Off with Spirobifluorene-Bridged Donor-π-Acceptor Chromophores Org. Lett. 2012, 14, 5282-5285
    • (2012) Org. Lett. , vol.14 , pp. 5282-5285
    • Xiao, H.1    Yin, H.2    Zhang, X.3
  • 16
    • 84880316662 scopus 로고    scopus 로고
    • Small D-π-A Systems with o-Phenylene-Bridged Accepting Units as Active Materials for Organic Photovoltaics
    • Leliège, A.; Grolleau, J.; Allain, M.; Blanchard, P.; Demeter, D.; Rousseau, T.; Roncali, J. Small D-π-A Systems with o-Phenylene-Bridged Accepting Units as Active Materials for Organic Photovoltaics Chem.-Eur. J. 2013, 19, 9948-9960
    • (2013) Chem. - Eur. J. , vol.19 , pp. 9948-9960
    • Leliège, A.1    Grolleau, J.2    Allain, M.3    Blanchard, P.4    Demeter, D.5    Rousseau, T.6    Roncali, J.7
  • 17
    • 80053590433 scopus 로고    scopus 로고
    • Air-Stable Triarylamine-Based Amorphous Polymer as Donor Material for Bulk-Heterojunction Organic Solar Cells
    • Yasuda, T.; Suzuki, T.; Takahashi, M.; Han, L. Air-Stable Triarylamine-Based Amorphous Polymer as Donor Material for Bulk-Heterojunction Organic Solar Cells Sol. Energy Mater. Sol. Cells 2011, 95, 3509-3515
    • (2011) Sol. Energy Mater. Sol. Cells , vol.95 , pp. 3509-3515
    • Yasuda, T.1    Suzuki, T.2    Takahashi, M.3    Han, L.4
  • 18
    • 70349270760 scopus 로고    scopus 로고
    • Triarylamine: A Promising Core Unit for Efficient Photovoltaic Materials
    • Ning, Z.; Tian, H. Triarylamine: A Promising Core Unit for Efficient Photovoltaic Materials Chem. Commun. 2009, 5483-5495
    • (2009) Chem. Commun. , pp. 5483-5495
    • Ning, Z.1    Tian, H.2
  • 23
    • 77149167298 scopus 로고    scopus 로고
    • Squaraine Compounds: Tailored Design and Synthesis Towards a Variety of Material Science Applications
    • Beverina, L.; Salice, P. Squaraine Compounds: Tailored Design and Synthesis Towards a Variety of Material Science Applications Eur. J. Org. Chem. 2010, 2010, 1207-1225
    • (2010) Eur. J. Org. Chem. , vol.2010 , pp. 1207-1225
    • Beverina, L.1    Salice, P.2
  • 25
    • 84857510123 scopus 로고    scopus 로고
    • Small Molecule Organic Semiconductors on the Move: Promises for Future Solar Energy Technology
    • Mishra, A.; Bäuerle, P. Small Molecule Organic Semiconductors on the Move: Promises for Future Solar Energy Technology Angew. Chem., Int. Ed. 2012, 51, 2020-2067
    • (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 2020-2067
    • Mishra, A.1    Bäuerle, P.2
  • 26
    • 84859953805 scopus 로고    scopus 로고
    • Small Molecule Semiconductors for High-Efficiency Organic Photovoltaics
    • Lin, Y.; Li, Y.; Zhan, X. Small Molecule Semiconductors for High-Efficiency Organic Photovoltaics Chem. Soc. Rev. 2012, 41, 4245-4272
    • (2012) Chem. Soc. Rev. , vol.41 , pp. 4245-4272
    • Lin, Y.1    Li, Y.2    Zhan, X.3
  • 27
    • 77954977681 scopus 로고    scopus 로고
    • A Weak Donor-Strong Acceptor Strategy to Design Ideal Polymers for Organic Solar Cells
    • Zhou, H.; Yang, L.; Stoneking, S.; You, W. A Weak Donor-Strong Acceptor Strategy to Design Ideal Polymers for Organic Solar Cells ACS Appl. Mater. Interfaces 2010, 2, 1377-1383
    • (2010) ACS Appl. Mater. Interfaces , vol.2 , pp. 1377-1383
    • Zhou, H.1    Yang, L.2    Stoneking, S.3    You, W.4
  • 28
    • 78349270539 scopus 로고    scopus 로고
    • Enhanced Photovoltaic Performance of Low-Bandgap Polymers with Deep LUMO Levels
    • Zhou, H.; Yang, L.; Price, S. C.; Knight, K. J.; You, W. Enhanced Photovoltaic Performance of Low-Bandgap Polymers with Deep LUMO Levels Angew. Chem., Int. Ed. 2010, 49, 7992-7995
    • (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 7992-7995
    • Zhou, H.1    Yang, L.2    Price, S.C.3    Knight, K.J.4    You, W.5
  • 29
    • 84055187666 scopus 로고    scopus 로고
    • Hole Transport in Triphenylamine Based OLED Devices: From Theoretical Modeling to Properties Prediction
    • Cias, P.; Slugovc, C.; Gescheidt, G. Hole Transport in Triphenylamine Based OLED Devices: From Theoretical Modeling to Properties Prediction J. Phys. Chem. A 2011, 115, 14519-14525
    • (2011) J. Phys. Chem. A , vol.115 , pp. 14519-14525
    • Cias, P.1    Slugovc, C.2    Gescheidt, G.3
  • 30
    • 77249157372 scopus 로고    scopus 로고
    • Organic Field Effect Transistors from Triarylamine Side-Chain Polymers
    • Huttner, S.; Sommer, M.; Steiner, U.; Thelakkat, M. Organic Field Effect Transistors from Triarylamine Side-Chain Polymers Appl. Phys. Lett. 2010, 96, 073503-1-073503-3
    • (2010) Appl. Phys. Lett. , vol.96 , pp. 0735031-0735033
    • Huttner, S.1    Sommer, M.2    Steiner, U.3    Thelakkat, M.4
  • 31
    • 0000754040 scopus 로고    scopus 로고
    • Synthesis of Unsymmetrical Triarylamines for Photonic Applications via One-Pot Palladium-Catalyzed Aminations
    • Thayumanavan, S.; Barlow, S.; Marder, S. R. Synthesis of Unsymmetrical Triarylamines for Photonic Applications via One-Pot Palladium-Catalyzed Aminations Chem. Mater. 1997, 9, 3231-3235
    • (1997) Chem. Mater. , vol.9 , pp. 3231-3235
    • Thayumanavan, S.1    Barlow, S.2    Marder, S.R.3
  • 32
    • 66549118967 scopus 로고    scopus 로고
    • The Role of C-H···O Hydrogen-Bonding Interactions in the Solid-State Packing of Squaraine Dyes
    • Lynch, D. E.; Byriel, K. A. The Role of C-H···O Hydrogen-Bonding Interactions in the Solid-State Packing of Squaraine Dyes Cryst. Eng. 1999, 2, 225-239
    • (1999) Cryst. Eng. , vol.2 , pp. 225-239
    • Lynch, D.E.1    Byriel, K.A.2
  • 33
    • 0035797056 scopus 로고    scopus 로고
    • Design and Synthesis of Stable Triarylamines for Hole-Transport Applications
    • Zhao, H.; Tanjutco, C.; Thayumanavan, S. Design and Synthesis of Stable Triarylamines for Hole-Transport Applications Tetrahedron Lett. 2001, 42, 4421-4424
    • (2001) Tetrahedron Lett. , vol.42 , pp. 4421-4424
    • Zhao, H.1    Tanjutco, C.2    Thayumanavan, S.3
  • 34
    • 0041914506 scopus 로고    scopus 로고
    • Building Blocks for n-Type Organic Electronics: Regiochemically Modulated Inversion of Majority Carrier Sign in Perfluoroarene-Modified Polythiophene Semiconductors
    • Facchetti, A.; Yoon, M.-H.; Stern, C. L.; Katz, H. E.; Marks, T. J. Building Blocks for n-Type Organic Electronics: Regiochemically Modulated Inversion of Majority Carrier Sign in Perfluoroarene-Modified Polythiophene Semiconductors Angew. Chem., Int. Ed. 2003, 42, 3900-3903
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 3900-3903
    • Facchetti, A.1    Yoon, M.-H.2    Stern, C.L.3    Katz, H.E.4    Marks, T.J.5
  • 35
    • 0037415118 scopus 로고    scopus 로고
    • N-Type Building Blocks for Organic Electronics: A Homologous Family of Fluorocarbon-Substituted Thiophene Oligomers with High Carrier Mobility
    • Facchetti, A.; Mushrush, M.; Katz, H. E.; Marks, T. J. n-Type Building Blocks for Organic Electronics: A Homologous Family of Fluorocarbon-Substituted Thiophene Oligomers with High Carrier Mobility Adv. Mater. 2003, 15, 33-38
    • (2003) Adv. Mater. , vol.15 , pp. 33-38
    • Facchetti, A.1    Mushrush, M.2    Katz, H.E.3    Marks, T.J.4
  • 36
    • 6444242950 scopus 로고    scopus 로고
    • Building Blocks for n-Type Molecular and Polymeric Electronics. Perfluoroalkyl- versus Alkyl-Functionalized Oligothiophenes (nT; N = 2-6). Systematics of Thin Film Microstructure, Semiconductor Performance, and Modeling of Majority Charge Injection in Field-Effect Transistors
    • Facchetti, A.; Mushrush, M.; Yoon, M.-H.; Hutchison, G. R.; Ratner, M. A.; Marks, T. J. Building Blocks for n-Type Molecular and Polymeric Electronics. Perfluoroalkyl- versus Alkyl-Functionalized Oligothiophenes (nT; n = 2-6). Systematics of Thin Film Microstructure, Semiconductor Performance, and Modeling of Majority Charge Injection in Field-Effect Transistors J. Am. Chem. Soc. 2004, 126, 13859-13874
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 13859-13874
    • Facchetti, A.1    Mushrush, M.2    Yoon, M.-H.3    Hutchison, G.R.4    Ratner, M.A.5    Marks, T.J.6
  • 37
    • 79952782380 scopus 로고    scopus 로고
    • Cyclopentadithiophene-Based Organic Semiconductors: Effect of Fluorinated Substituents on Electrochemical and Charge Transport Properties
    • Reddy, J. S.; Kale, T.; Balaji, G.; Chandrasekaran, A.; Thayumanavan, S. Cyclopentadithiophene-Based Organic Semiconductors: Effect of Fluorinated Substituents on Electrochemical and Charge Transport Properties J. Phys. Chem. Lett. 2011, 2, 648-654
    • (2011) J. Phys. Chem. Lett. , vol.2 , pp. 648-654
    • Reddy, J.S.1    Kale, T.2    Balaji, G.3    Chandrasekaran, A.4    Thayumanavan, S.5
  • 38
    • 33646540412 scopus 로고    scopus 로고
    • Fluorocarbon-Modified Organic Semiconductors: Molecular Architecture, Electronic, and Crystal Structure Tuning of Arene- versus Fluoroarene-Thiophene Oligomer Thin-Film Properties
    • Yoon, M.-H.; Facchetti, A.; Stern, C. E.; Marks, T. J. Fluorocarbon-Modified Organic Semiconductors: Molecular Architecture, Electronic, and Crystal Structure Tuning of Arene- versus Fluoroarene-Thiophene Oligomer Thin-Film Properties J. Am. Chem. Soc. 2006, 128, 5792-5801
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 5792-5801
    • Yoon, M.-H.1    Facchetti, A.2    Stern, C.E.3    Marks, T.J.4
  • 39
    • 35348920070 scopus 로고    scopus 로고
    • High-Performance n-Channel Carbonyl-Functionalized Quaterthiophene Semiconductors: Thin-Film Transistor Response and Majority Carrier Type Inversion via Simple Chemical Protection/Deprotection
    • Yoon, M.-H.; DiBenedetto, S. A.; Russell, M. T.; Facchetti, A.; Marks, T. J. High-Performance n-Channel Carbonyl-Functionalized Quaterthiophene Semiconductors: Thin-Film Transistor Response and Majority Carrier Type Inversion via Simple Chemical Protection/Deprotection Chem. Mater. 2007, 19, 4864-4881
    • (2007) Chem. Mater. , vol.19 , pp. 4864-4881
    • Yoon, M.-H.1    Dibenedetto, S.A.2    Russell, M.T.3    Facchetti, A.4    Marks, T.J.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.