메뉴 건너뛰기




Volumn 15, Issue 12, 2014, Pages 3521-3528

Hydrogen-bonded diketopyrrolopyrrole (DPP) pigments as organic semiconductors

Author keywords

DFT calculations; Diketopyrrolopyrrole; Hydrogen bonding; Organic field effect transistors; Organic pigments

Indexed keywords

CARRIER MOBILITY; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; HYDROGEN; HYDROGEN BONDS; MOLECULES; SEMICONDUCTING POLYMERS; TRANSISTORS;

EID: 84908313917     PISSN: 15661199     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.orgel.2014.09.038     Document Type: Article
Times cited : (104)

References (43)
  • 1
    • 33846269194 scopus 로고    scopus 로고
    • Some aspects of organic pigments
    • Z. Hao, and A. Iqbal Some aspects of organic pigments Chem. Soc. Rev. 26 1997 203
    • (1997) Chem. Soc. Rev. , vol.26 , pp. 203
    • Hao, Z.1    Iqbal, A.2
  • 3
    • 0001218664 scopus 로고    scopus 로고
    • Correlation between crystal and electronic structures in diketopyrrolopyrrole pigments as viewed from exciton coupling effects
    • J. Mizuguchi Correlation between crystal and electronic structures in diketopyrrolopyrrole pigments as viewed from exciton coupling effects J. Phys. Chem. A. 104 2000 1817 1821
    • (2000) J. Phys. Chem. A. , vol.104 , pp. 1817-1821
    • Mizuguchi, J.1
  • 4
    • 0002953693 scopus 로고
    • Hydrogen bonding and the deliberate design of organic crystal structures
    • G.R. Desiraju Hydrogen bonding and the deliberate design of organic crystal structures Mol. Cryst. Liq. Cryst. 211 1992 63 74
    • (1992) Mol. Cryst. Liq. Cryst. , vol.211 , pp. 63-74
    • Desiraju, G.R.1
  • 5
    • 0041694107 scopus 로고    scopus 로고
    • Crystal engineering. from molecules to materials
    • G.R. Desiraju Crystal engineering. From molecules to materials J. Mol. Struct. 656 2003 5 15
    • (2003) J. Mol. Struct. , vol.656 , pp. 5-15
    • Desiraju, G.R.1
  • 6
    • 79953895976 scopus 로고    scopus 로고
    • Reflections on the hydrogen bond in crystal engineering
    • G.R. Desiraju Reflections on the hydrogen bond in crystal engineering Cryst. Growth Des. 11 2011 896 898
    • (2011) Cryst. Growth Des. , vol.11 , pp. 896-898
    • Desiraju, G.R.1
  • 7
    • 69949161547 scopus 로고    scopus 로고
    • High-performance air-stable n-channel organic thin film transistors based on halogenated perylene bisimide semiconductors
    • R. Schmidt, J.H. Oh, Y.-S. Sun, M. Deppisch, A.-M. Krause, and K. Radacki High-performance air-stable n-channel organic thin film transistors based on halogenated perylene bisimide semiconductors J. Am. Chem. Soc. 131 2009 6215 6228
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 6215-6228
    • Schmidt, R.1    Oh, J.H.2    Sun, Y.-S.3    Deppisch, M.4    Krause, A.-M.5    Radacki, K.6
  • 8
    • 74849117933 scopus 로고    scopus 로고
    • A crystal-engineered hydrogen-bonded octachloroperylene diimide with a twisted core: An n-channel organic semiconductor
    • M. Gsänger, J.H. Oh, M. Könemann, H.W. Höffken, A.-M. Krause, and Z. Bao A crystal-engineered hydrogen-bonded octachloroperylene diimide with a twisted core: an n-channel organic semiconductor Angew. Chem. 49 2010 740 743
    • (2010) Angew. Chem. , vol.49 , pp. 740-743
    • Gsänger, M.1    Oh, J.H.2    Könemann, M.3    Höffken, H.W.4    Krause, A.-M.5    Bao, Z.6
  • 9
  • 12
    • 84873141998 scopus 로고    scopus 로고
    • Recent advances in the development of semiconducting DPP-containing polymers for transistor applications
    • C.B. Nielsen, M. Turbiez, and I. McCulloch Recent advances in the development of semiconducting DPP-containing polymers for transistor applications Adv. Mater. 25 2012 1859 1880
    • (2012) Adv. Mater. , vol.25 , pp. 1859-1880
    • Nielsen, C.B.1    Turbiez, M.2    McCulloch, I.3
  • 13
    • 84857729602 scopus 로고    scopus 로고
    • Diketopyrrolopyrrole (DPP)-based materials for organic photovoltaics
    • S. Qu, and H. Tian Diketopyrrolopyrrole (DPP)-based materials for organic photovoltaics Chem. Commun. 48 2012 3039 3051
    • (2012) Chem. Commun. , vol.48 , pp. 3039-3051
    • Qu, S.1    Tian, H.2
  • 14
    • 55049085310 scopus 로고    scopus 로고
    • Organic field-effect transistor devices based on latent pigments of unsubstituted diketopyrrolopyrrole or quinacridone
    • H. Yanagisawa, J. Mizuguchi, S. Aramaki, and Y. Sakai Organic field-effect transistor devices based on latent pigments of unsubstituted diketopyrrolopyrrole or quinacridone Jpn. J. Appl. Phys. 47 2008 4728 4731
    • (2008) Jpn. J. Appl. Phys. , vol.47 , pp. 4728-4731
    • Yanagisawa, H.1    Mizuguchi, J.2    Aramaki, S.3    Sakai, Y.4
  • 15
    • 84867094261 scopus 로고    scopus 로고
    • Inversion of dominant polarity in ambipolar polydiketopyrrolopyrrole with thermally removable groups
    • J. Lee, A.-R. Han, J. Hong, J.H. Seo, J.H. Oh, and C. Yang Inversion of dominant polarity in ambipolar polydiketopyrrolopyrrole with thermally removable groups Adv. Funct. Mater. 22 2012 4128 4138
    • (2012) Adv. Funct. Mater. , vol.22 , pp. 4128-4138
    • Lee, J.1    Han, A.-R.2    Hong, J.3    Seo, J.H.4    Oh, J.H.5    Yang, C.6
  • 16
    • 79952231623 scopus 로고    scopus 로고
    • π-conjugated polymers for organic electronics and photovoltaic cell applications
    • A. Facchetti π-conjugated polymers for organic electronics and photovoltaic cell applications Chem. Mater. 23 2011 733 758
    • (2011) Chem. Mater. , vol.23 , pp. 733-758
    • Facchetti, A.1
  • 17
    • 77953890426 scopus 로고    scopus 로고
    • Electroactive materials for organic electronics: Preparation strategies, structural aspects and characterization techniques
    • A. Pron, P. Gawrys, M. Zagorska, D. Djurado, and R. Demadrille Electroactive materials for organic electronics: preparation strategies, structural aspects and characterization techniques Chem. Soc. Rev. 39 2010 2577 2632
    • (2010) Chem. Soc. Rev. , vol.39 , pp. 2577-2632
    • Pron, A.1    Gawrys, P.2    Zagorska, M.3    Djurado, D.4    Demadrille, R.5
  • 18
    • 84880588190 scopus 로고    scopus 로고
    • Hydrogen-bonds in molecular solids - From biological systems to organic electronics
    • E.D. Głowacki, M. Irimia-Vladu, S. Bauer, and N.S. Sariciftci Hydrogen-bonds in molecular solids - from biological systems to organic electronics J. Mater. Chem. B. 1 2013 3742 3753
    • (2013) J. Mater. Chem. B. , vol.1 , pp. 3742-3753
    • Głowacki, E.D.1    Irimia-Vladu, M.2    Bauer, S.3    Sariciftci, N.S.4
  • 19
    • 67849083473 scopus 로고    scopus 로고
    • Novel poly(phenylene ethynylene)-type conjugated polymers containing diketopyrrolopyrrole or triphenylpyrazoline units in the main chain: Synthesis, characterization and photophysical properties
    • G. Zhang, K. Liu, Y. Li, and M. Yang Novel poly(phenylene ethynylene)-type conjugated polymers containing diketopyrrolopyrrole or triphenylpyrazoline units in the main chain: synthesis, characterization and photophysical properties Polym. Int. 58 2009 665 673
    • (2009) Polym. Int. , vol.58 , pp. 665-673
    • Zhang, G.1    Liu, K.2    Li, Y.3    Yang, M.4
  • 20
    • 79958859853 scopus 로고    scopus 로고
    • Electrochemical considerations for determining absolute frontier orbital energy levels of conjugated polymers for solar cell applications
    • C.M. Cardona, W. Li, A.E. Kaifer, D. Stockdale, and G.C. Bazan Electrochemical considerations for determining absolute frontier orbital energy levels of conjugated polymers for solar cell applications Adv. Mater. 23 2011 2367 2371
    • (2011) Adv. Mater. , vol.23 , pp. 2367-2371
    • Cardona, C.M.1    Li, W.2    Kaifer, A.E.3    Stockdale, D.4    Bazan, G.C.5
  • 21
    • 0027885918 scopus 로고
    • Thin anodic oxide layers on aluminium and other valve metals: High field regime
    • M.M. Lohrengel Thin anodic oxide layers on aluminium and other valve metals: high field regime Mater. Sci. Eng. R. 11 1993 243 294
    • (1993) Mater. Sci. Eng. R. , vol.11 , pp. 243-294
    • Lohrengel, M.M.1
  • 22
    • 82955188705 scopus 로고    scopus 로고
    • Anodized aluminum oxide thin films for room-temperature-processed, flexible, low-voltage organic non-volatile memory elements with excellent charge retention
    • M. Kaltenbrunner, P. Stadler, R. Schwödiauer, A.W. Hassel, N.S. Sariciftci, and S. Bauer Anodized aluminum oxide thin films for room-temperature-processed, flexible, low-voltage organic non-volatile memory elements with excellent charge retention Adv. Mater. 23 2011 4892 4896
    • (2011) Adv. Mater. , vol.23 , pp. 4892-4896
    • Kaltenbrunner, M.1    Stadler, P.2    Schwödiauer, R.3    Hassel, A.W.4    Sariciftci, N.S.5    Bauer, S.6
  • 23
    • 79251526860 scopus 로고    scopus 로고
    • High-mobility copper-phthalocyanine field-effect transistors with tetratetracontane passivation layer and organic metal contacts
    • M. Kraus, S. Richler, A. Opitz, W. Brütting, S. Haas, and T. Hasegawa High-mobility copper-phthalocyanine field-effect transistors with tetratetracontane passivation layer and organic metal contacts J. Appl. Phys. 107 2010 094503
    • (2010) J. Appl. Phys. , vol.107 , pp. 094503
    • Kraus, M.1    Richler, S.2    Opitz, A.3    Brütting, W.4    Haas, S.5    Hasegawa, T.6
  • 24
    • 84861864716 scopus 로고    scopus 로고
    • Bipolar charge transport in organic field-effect transistors: Enabling high mobilities and transport of photo-generated charge carriers by a molecular passivation layer
    • A. Opitz, M. Horlet, M. Kiwull, J. Wagner, M. Kraus, and W. Brütting Bipolar charge transport in organic field-effect transistors: enabling high mobilities and transport of photo-generated charge carriers by a molecular passivation layer Org. Electron. 13 2012 1614 1622
    • (2012) Org. Electron. , vol.13 , pp. 1614-1622
    • Opitz, A.1    Horlet, M.2    Kiwull, M.3    Wagner, J.4    Kraus, M.5    Brütting, W.6
  • 25
    • 0001501021 scopus 로고
    • Electronic spectra of 1,4-diketo-3,6-diphenyl-pyrrolo-[3,4-c]-pyrrole in the solid state
    • J. Mizuguchi, and G. Rihs Electronic spectra of 1,4-diketo-3,6-diphenyl-pyrrolo-[3,4-c]-pyrrole in the solid state Ber. Bunsen-Ges. Phys. Chem. 96 1991 597 606
    • (1991) Ber. Bunsen-Ges. Phys. Chem. , vol.96 , pp. 597-606
    • Mizuguchi, J.1    Rihs, G.2
  • 26
    • 0030835189 scopus 로고    scopus 로고
    • DMSO solvent induced photochemistry in highly photostable compounds. The role of intermolecular hydrogen bonding
    • P.F. Mcgarry, S. Jockusch, Y. Fujiwara, N.A. Kaprinidis, and N.J. Turro DMSO solvent induced photochemistry in highly photostable compounds. The role of intermolecular hydrogen bonding J. Phys. Chem. A 101 1997 764 767
    • (1997) J. Phys. Chem. A , vol.101 , pp. 764-767
    • McGarry, P.F.1    Jockusch, S.2    Fujiwara, Y.3    Kaprinidis, N.A.4    Turro, N.J.5
  • 27
    • 84944815031 scopus 로고
    • Structures of 3,6-diphenylpyrrolo[3,4-c]pyrrole-1,4-dione and 2,5-dimethyl-3,6-diphenylpyrrolo[3,4-c]pyrrole-1,4-dione
    • J. Mizuguchi, A. Grubenmann, G. Wooden, and G. Rihs Structures of 3,6-diphenylpyrrolo[3,4-c]pyrrole-1,4-dione and 2,5-dimethyl-3,6-diphenylpyrrolo[3,4-c]pyrrole-1,4-dione Acta Crystallogr., Sect. B: Struct. Sci. 48 1992 696 700
    • (1992) Acta Crystallogr., Sect. B: Struct. Sci. , vol.48 , pp. 696-700
    • Mizuguchi, J.1    Grubenmann, A.2    Wooden, G.3    Rihs, G.4
  • 28
    • 0000302404 scopus 로고
    • Structures of 3,6-bis(3-chlorophenyl)pyrrolo[3,4- c ]pyrrole-1,4-dione and 3,6-bis(4-chlorophenyl)pyrrolo[3,4- c ]pyrrole-1,4-dione
    • J. Mizuguchi, A. Grubenmann, and G. Rihs Structures of 3,6-bis(3-chlorophenyl)pyrrolo[3,4- c ]pyrrole-1,4-dione and 3,6-bis(4-chlorophenyl)pyrrolo[3,4- c ]pyrrole-1,4-dione Acta Crystallogr., Sect. B: Struct. Sci. 49 1993 1056 1060
    • (1993) Acta Crystallogr., Sect. B: Struct. Sci. , vol.49 , pp. 1056-1060
    • Mizuguchi, J.1    Grubenmann, A.2    Rihs, G.3
  • 29
    • 0033554710 scopus 로고    scopus 로고
    • Two-dimensional charge transport in self-organized, high-mobility conjugated polymers
    • H. Sirringhaus, P.J. Brown, K. Bechgaard, and A.J.H. Spiering Two-dimensional charge transport in self-organized, high-mobility conjugated polymers Nature 401 1999 685 688
    • (1999) Nature , vol.401 , pp. 685-688
    • Sirringhaus, H.1    Brown, P.J.2    Bechgaard, K.3    Spiering, A.J.H.4
  • 30
    • 34248339106 scopus 로고    scopus 로고
    • Electron and ambipolar transport in organic field-effect transistors
    • J. Zaumseil, and H. Sirringhaus Electron and ambipolar transport in organic field-effect transistors Chem. Rev. 107 2007 1296 1323
    • (2007) Chem. Rev. , vol.107 , pp. 1296-1323
    • Zaumseil, J.1    Sirringhaus, H.2
  • 31
    • 0000138156 scopus 로고
    • Band-hopping mobility transition in naphthalene and deuterated naphthalene
    • L.B. Schein, and A.R. McGhie Band-hopping mobility transition in naphthalene and deuterated naphthalene Phys. Rev. B. 20 1979 1631 1639
    • (1979) Phys. Rev. B. , vol.20 , pp. 1631-1639
    • Schein, L.B.1    McGhie, A.R.2
  • 32
    • 21144473420 scopus 로고
    • Electron transfer reactions in chemistry. Theory and experiment
    • R.A. Marcus Electron transfer reactions in chemistry. Theory and experiment Rev. Mod. Phys. 65 1993 599 610
    • (1993) Rev. Mod. Phys. , vol.65 , pp. 599-610
    • Marcus, R.A.1
  • 35
    • 0000189651 scopus 로고
    • Density-functional thermochemistry. III. The role of exact exchange
    • A.D. Becke Density-functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 98 1993 5648
    • (1993) J. Chem. Phys. , vol.98 , pp. 5648
    • Becke, A.D.1
  • 36
    • 33751157732 scopus 로고
    • Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields
    • P.J. Stephens, F.J. Devlin, C.F. Chabalowski, and M.J. Frisch Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields J. Phys. Chem. 98 1994 11623 11627
    • (1994) J. Phys. Chem. , vol.98 , pp. 11623-11627
    • Stephens, P.J.1    Devlin, F.J.2    Chabalowski, C.F.3    Frisch, M.J.4
  • 37
    • 22744441344 scopus 로고    scopus 로고
    • Design of density functionals that are broadly accurate for thermochemistry, thermochemical kinetics, and nonbonded interactions
    • Y. Zhao, and D.G. Truhlar Design of density functionals that are broadly accurate for thermochemistry, thermochemical kinetics, and nonbonded interactions J. Phys. Chem. A. 109 2005 5656 5667
    • (2005) J. Phys. Chem. A. , vol.109 , pp. 5656-5667
    • Zhao, Y.1    Truhlar, D.G.2
  • 38
    • 79952943559 scopus 로고    scopus 로고
    • Effect of the damping function in dispersion corrected density functional theory
    • S. Grimme, S. Ehrlich, and L. Goerigk Effect of the damping function in dispersion corrected density functional theory J. Comput. Chem. 32 2011 1456 1465
    • (2011) J. Comput. Chem. , vol.32 , pp. 1456-1465
    • Grimme, S.1    Ehrlich, S.2    Goerigk, L.3
  • 39
    • 26244461462 scopus 로고    scopus 로고
    • Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy
    • F. Weigend, and R. Ahlrichs Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: design and assessment of accuracy Phys. Chem. Chem. Phys. 7 2005 3297 3305
    • (2005) Phys. Chem. Chem. Phys. , vol.7 , pp. 3297-3305
    • Weigend, F.1    Ahlrichs, R.2
  • 41
    • 0035857418 scopus 로고    scopus 로고
    • Electronic structure of the pentacene single crystal: Relation to transport properties
    • J. Cornil, J.P. Calbert, and J.L. Brédas Electronic structure of the pentacene single crystal: relation to transport properties J. Am. Chem. Soc. 123 2001 1250 1251
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 1250-1251
    • Cornil, J.1    Calbert, J.P.2    Brédas, J.L.3
  • 42
    • 79955703065 scopus 로고    scopus 로고
    • Property-optimized gaussian basis sets for molecular response calculations
    • D. Rappoport, and F. Furche Property-optimized gaussian basis sets for molecular response calculations J. Chem. Phys. 133 2010 134105
    • (2010) J. Chem. Phys. , vol.133 , pp. 134105
    • Rappoport, D.1    Furche, F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.