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Volumn 118, Issue 1, 2014, Pages 657-669

Polymorphism in bulk and thin films: The curious case of dithiophene-DPP(Boc)-dithiophene

Author keywords

[No Author keywords available]

Indexed keywords

HIRSHFELD SURFACES; INTERFACE MORPHOLOGIES; INTERMOLECULAR INTERACTIONS; LATTICE ENERGY CALCULATIONS; STRUCTURAL CHARACTERIZATION; STRUCTURE PROPERTY RELATIONSHIPS; SUPRAMOLECULAR ARCHITECTURES; X-RAY DIFFRACTION DATA;

EID: 84892581504     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp410824u     Document Type: Article
Times cited : (25)

References (67)
  • 1
    • 79952139395 scopus 로고    scopus 로고
    • Polymorphism - A Perspective
    • Bernstein, J. Polymorphism-a Perspective Cryst. Growth Des. 2011, 11, 632-650
    • (2011) Cryst. Growth Des. , vol.11 , pp. 632-650
    • Bernstein, J.1
  • 2
    • 0040364227 scopus 로고
    • Polymorphism and the Investigation of Structure-Property Relations in Organic Solids
    • Garbarczyk, J. B. Jones, D. W. Oxford University Press: Oxford, U.K
    • Bernstein, J., Polymorphism and the Investigation of Structure-Property Relations in Organic Solids. In Organic Crystal Chemistry; Garbarczyk, J. B.; Jones, D. W., Eds.; Oxford University Press: Oxford, U.K., 1991.
    • (1991) Organic Crystal Chemistry
    • Bernstein, J.1
  • 4
    • 84883892563 scopus 로고    scopus 로고
    • Polymorphism, What It Is and How to Identify It: A Systematic Review
    • Fromm, K.; Crochet, A.; Chanez, C.-L.; Brog, J.-P. Polymorphism, What It Is and How to Identify It: A Systematic Review RSC Adv. 2013, 3, 16905-16931
    • (2013) RSC Adv. , vol.3 , pp. 16905-16931
    • Fromm, K.1    Crochet, A.2    Chanez, C.-L.3    Brog, J.-P.4
  • 5
    • 84875174950 scopus 로고    scopus 로고
    • Special Feature Section: Polymorphism and Crystallisation
    • Laird, T. Special Feature Section: Polymorphism and Crystallisation Org. Process Res. Dev. 2013, 17, 443-444
    • (2013) Org. Process Res. Dev. , vol.17 , pp. 443-444
    • Laird, T.1
  • 6
    • 72449157428 scopus 로고    scopus 로고
    • Polymorphism in Processes of Crystallization in Solution: A Practical Review
    • Mangin, D.; Puel, F.; Veesler, S. Polymorphism in Processes of Crystallization in Solution: A Practical Review Org. Process Res. Dev. 2009, 13, 1241-1253
    • (2009) Org. Process Res. Dev. , vol.13 , pp. 1241-1253
    • Mangin, D.1    Puel, F.2    Veesler, S.3
  • 7
    • 61849114738 scopus 로고    scopus 로고
    • Computed Crystal Energy Landscapes for Understanding and Predicting Organic Crystal Structures and Polymorphism
    • Price, S. L. Computed Crystal Energy Landscapes for Understanding and Predicting Organic Crystal Structures and Polymorphism Acc. Chem. Res. 2008, 42, 117-126
    • (2008) Acc. Chem. Res. , vol.42 , pp. 117-126
    • Price, S.L.1
  • 8
    • 38449102844 scopus 로고    scopus 로고
    • Editorial: Facets of Polymorphism in Crystals
    • Matzger, A. J. Editorial: Facets of Polymorphism in Crystals Cryst. Growth Des. 2008, 8, 2-2
    • (2008) Cryst. Growth Des. , vol.8 , pp. 2-2
    • Matzger, A.J.1
  • 10
  • 14
    • 79953887333 scopus 로고    scopus 로고
    • Structure Solution of the 6,13-Pentacenequinone Surface-Induced Polymorph by Combining X-Ray Diffraction Reciprocal-Space Mapping and Theoretical Structure Modeling
    • Salzmann, I.; Nabok, D.; Oehzelt, M.; Duhm, S.; Moser, A.; Heimel, G.; Puschnig, P.; Ambrosch-Draxl, C.; Rabe, J. R. P.; Koch, N. Structure Solution of the 6,13-Pentacenequinone Surface-Induced Polymorph by Combining X-Ray Diffraction Reciprocal-Space Mapping and Theoretical Structure Modeling Cryst. Growth Des. 2011, 11, 600-606
    • (2011) Cryst. Growth Des. , vol.11 , pp. 600-606
    • Salzmann, I.1    Nabok, D.2    Oehzelt, M.3    Duhm, S.4    Moser, A.5    Heimel, G.6    Puschnig, P.7    Ambrosch-Draxl, C.8    Rabe, J.R.P.9    Koch, N.10
  • 17
    • 0032026773 scopus 로고    scopus 로고
    • Crystal Growth, Structure, and Electronic Band Structure of A-4t Polymorphs
    • Siegrist, T.; Kloc, C.; Laudise, R. A.; Katz, H. E.; Haddon, R. C. Crystal Growth, Structure, and Electronic Band Structure of A-4t Polymorphs Adv. Mater. 1998, 10, 379-382
    • (1998) Adv. Mater. , vol.10 , pp. 379-382
    • Siegrist, T.1    Kloc, C.2    Laudise, R.A.3    Katz, H.E.4    Haddon, R.C.5
  • 18
    • 33645308778 scopus 로고    scopus 로고
    • Low-Temperature Structure of Rubrene Single Crystals Grown by Vapor Transport
    • Jurchescu, O. D.; Meetsma, A.; Palstra, T. T. M. Low-Temperature Structure of Rubrene Single Crystals Grown by Vapor Transport Acta Crystallogr., Sect. B 2006, 62, 330-334
    • (2006) Acta Crystallogr., Sect. B , vol.62 , pp. 330-334
    • Jurchescu, O.D.1    Meetsma, A.2    Palstra, T.T.M.3
  • 20
    • 84877796359 scopus 로고    scopus 로고
    • Diketopyrrolopyrrole: A Versatile Building Block for Organic Photovoltaic Materials
    • Chandran, D.; Lee, K.-S. Diketopyrrolopyrrole: A Versatile Building Block for Organic Photovoltaic Materials Macromol. Res. 2013, 21, 272-283
    • (2013) Macromol. Res. , vol.21 , pp. 272-283
    • Chandran, D.1    Lee, K.-S.2
  • 22
    • 79958748184 scopus 로고    scopus 로고
    • Diketo-Pyrrolo-Pyrrole-Based Medium Band Gap Copolymers for Efficient Plastic Solar Cells: Morphology, Transport, and Composition-Dependent Photovoltaic Behavior
    • Chen, L.; Deng, D.; Nan, Y.; Shi, M.; Chan, P. K. L.; Chen, H. Diketo-Pyrrolo-Pyrrole-Based Medium Band Gap Copolymers for Efficient Plastic Solar Cells: Morphology, Transport, and Composition-Dependent Photovoltaic Behavior J. Phys. Chem. C 2011, 115, 11282-11292
    • (2011) J. Phys. Chem. C , vol.115 , pp. 11282-11292
    • Chen, L.1    Deng, D.2    Nan, Y.3    Shi, M.4    Chan, P.K.L.5    Chen, H.6
  • 23
    • 84857729602 scopus 로고    scopus 로고
    • Diketopyrrolopyrrole (Dpp)-Based Materials for Organic Photovoltaics
    • Qu, S.; Tian, H. Diketopyrrolopyrrole (Dpp)-Based Materials for Organic Photovoltaics Chem. Commun. 2012, 48, 3039-3051
    • (2012) Chem. Commun. , vol.48 , pp. 3039-3051
    • Qu, S.1    Tian, H.2
  • 24
    • 84864758855 scopus 로고    scopus 로고
    • Optical Properties of Oligothiophene Substituted Diketopyrrolopyrrole Derivatives in the Solid Phase: Joint J- and H- Type Aggregation
    • Kirkus, M.; Wang, L.; Mothy, S.; Beljonne, D.; Cornil, J.; Janssen, R. A. J.; Meskers, S. C. J. Optical Properties of Oligothiophene Substituted Diketopyrrolopyrrole Derivatives in the Solid Phase: Joint J- and H- Type Aggregation J. Phys. Chem. A 2012, 116, 7927-7936
    • (2012) J. Phys. Chem. A , vol.116 , pp. 7927-7936
    • Kirkus, M.1    Wang, L.2    Mothy, S.3    Beljonne, D.4    Cornil, J.5    Janssen, R.A.J.6    Meskers, S.C.J.7
  • 25
    • 79952596606 scopus 로고    scopus 로고
    • Thieno[3,2-B]Thiophene-Diketopyrrolopyrrole-Containing Polymers for High-Performance Organic Field-Effect Transistors and Organic Photovoltaic Devices
    • Bronstein, H.; Chen, Z.; Ashraf, R. S.; Zhang, W.; Du, J.; Durrant, J. R.; Shakya Tuladhar, P.; Song, K.; Watkins, S. E.; Geerts, Y. Thieno[3,2-B]Thiophene-Diketopyrrolopyrrole-Containing Polymers for High-Performance Organic Field-Effect Transistors and Organic Photovoltaic Devices J. Am. Chem. Soc. 2011, 133, 3272-3275
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 3272-3275
    • Bronstein, H.1    Chen, Z.2    Ashraf, R.S.3    Zhang, W.4    Du, J.5    Durrant, J.R.6    Shakya Tuladhar, P.7    Song, K.8    Watkins, S.E.9    Geerts, Y.10
  • 30
    • 0001752768 scopus 로고    scopus 로고
    • The Cambridge Structural Database: A Quarter of a Million Crystal Structures and Rising
    • Allen, F. The Cambridge Structural Database: A Quarter of a Million Crystal Structures and Rising Acta Crystallogr., Sect. B 2002, 58, 380-388
    • (2002) Acta Crystallogr., Sect. B , vol.58 , pp. 380-388
    • Allen, F.1
  • 31
    • 61749091130 scopus 로고    scopus 로고
    • Lessons on the Discovery and Assignment of Polymorphs, Highlighted by the Case of the Latent Pigment Dpp-Boc
    • Maclean, E. J.; Tremayne, M.; Kariuki, B. M.; Cameron, J. R. A.; Roberts, M. A.; Harris, K. D. M. Lessons on the Discovery and Assignment of Polymorphs, Highlighted by the Case of the Latent Pigment Dpp-Boc Cryst. Growth Des. 2009, 9, 853-857
    • (2009) Cryst. Growth Des. , vol.9 , pp. 853-857
    • Maclean, E.J.1    Tremayne, M.2    Kariuki, B.M.3    Cameron, J.R.A.4    Roberts, M.A.5    Harris, K.D.M.6
  • 32
    • 37549046466 scopus 로고    scopus 로고
    • Structure Determination from Powder Diffraction Data
    • David, W. I. F.; Shankland, K. Structure Determination from Powder Diffraction Data Acta Crystallogr., Sect. A 2008, 64, 52-64
    • (2008) Acta Crystallogr., Sect. A , vol.64 , pp. 52-64
    • David, W.I.F.1    Shankland, K.2
  • 33
    • 9144257887 scopus 로고    scopus 로고
    • How to Determine Structures When Single Crystals Cannot Be Grown: Opportunities for Structure Determination of Molecular Materials Using Powder Diffraction Data
    • Harris, K. D. M.; Cheung, E. Y. How to Determine Structures When Single Crystals Cannot Be Grown: Opportunities for Structure Determination of Molecular Materials Using Powder Diffraction Data Chem. Soc. Rev. 2004, 33, 526-538
    • (2004) Chem. Soc. Rev. , vol.33 , pp. 526-538
    • Harris, K.D.M.1    Cheung, E.Y.2
  • 34
    • 38549167909 scopus 로고    scopus 로고
    • Ab-Initio Crystal Structure Determination from X-ray Powder Diffraction Data
    • Mukherjee, A. K. Ab-Initio Crystal Structure Determination from X-ray Powder Diffraction Data J. Indian Inst. Sci. 2007, 87, 221-235
    • (2007) J. Indian Inst. Sci. , vol.87 , pp. 221-235
    • Mukherjee, A.K.1
  • 35
    • 0034236750 scopus 로고    scopus 로고
    • Structural Understanding of a Polymorphic System by Structure Solution and Refinement from Powder X-Ray Diffraction Data: The A and B Phases of the Latent Pigment Dpp-Boc
    • Maclean, E. J.; Tremayne, M.; Kariuki, B. M.; Harris, K. D. M.; Iqbal, A. F. M.; Hao, Z. Structural Understanding of a Polymorphic System by Structure Solution and Refinement from Powder X-Ray Diffraction Data: The A and B Phases of the Latent Pigment Dpp-Boc J. Chem. Soc., Perkin Trans. 2 2000, 1513-1519
    • (2000) J. Chem. Soc., Perkin Trans. 2 , pp. 1513-1519
    • Maclean, E.J.1    Tremayne, M.2    Kariuki, B.M.3    Harris, K.D.M.4    Iqbal, A.F.M.5    Hao, Z.6
  • 36
    • 49449111408 scopus 로고    scopus 로고
    • A Low Band Gap, Solution Processable Oligothiophene with a Diketopyrrolopyrrole Core for Use in Organic Solar Cells
    • Tamayo, A. B.; Walker, B.; Nguyen, T.-Q. A Low Band Gap, Solution Processable Oligothiophene with a Diketopyrrolopyrrole Core for Use in Organic Solar Cells J. Phys. Chem. C 2008, 112, 11545-11551
    • (2008) J. Phys. Chem. C , vol.112 , pp. 11545-11551
    • Tamayo, A.B.1    Walker, B.2    Nguyen, T.-Q.3
  • 37
    • 6344241177 scopus 로고    scopus 로고
    • Powder Pattern Indexing with the Dichotomy Method
    • Boultif, A.; Louër, D. Powder Pattern Indexing with the Dichotomy Method J. Appl. Crystallogr. 2004, 37, 724-731
    • (2004) J. Appl. Crystallogr. , vol.37 , pp. 724-731
    • Boultif, A.1    Louër, D.2
  • 38
    • 0026368044 scopus 로고
    • Indexing of Powder Diffraction Patterns for Low-Symmetry Lattices by the Successive Dichotomy Method
    • Boultif, A.; Louër, D. Indexing of Powder Diffraction Patterns for Low-Symmetry Lattices by the Successive Dichotomy Method J. Appl. Crystallogr. 1991, 24, 987-993
    • (1991) J. Appl. Crystallogr. , vol.24 , pp. 987-993
    • Boultif, A.1    Louër, D.2
  • 40
    • 0002211129 scopus 로고
    • A Profile Refinement Method for Nuclear and Magnetic Structures
    • Rietveld, H. A Profile Refinement Method for Nuclear and Magnetic Structures J. Appl. Crystallogr. 1969, 2, 65-71
    • (1969) J. Appl. Crystallogr. , vol.2 , pp. 65-71
    • Rietveld, H.1
  • 41
    • 0001632607 scopus 로고
    • Line Profiles of Neutron Powder-Diffraction Peaks for Structure Refinement
    • Rietveld, H. Line Profiles of Neutron Powder-Diffraction Peaks for Structure Refinement Acta Crystallogr. 1967, 22, 151-152
    • (1967) Acta Crystallogr. , vol.22 , pp. 151-152
    • Rietveld, H.1
  • 42
    • 84892582281 scopus 로고    scopus 로고
    • General Structure Analysis System (GSAS); Report LAUR 86-748; Los Alamos National Laboratory: Los Alamos, NM
    • Larson, A.; Von Dreele, R. General Structure Analysis System (GSAS); Report LAUR 86-748; Los Alamos National Laboratory: Los Alamos, NM, 2000.
    • (2000)
    • Larson, A.1    Von Dreele, R.2
  • 43
    • 0035073837 scopus 로고    scopus 로고
    • EXPGUI, a Graphical User Interface for GSAS
    • Toby, B. H. EXPGUI, a Graphical User Interface for GSAS J. Appl. Crystallogr. 2001, 34, 210-213
    • (2001) J. Appl. Crystallogr. , vol.34 , pp. 210-213
    • Toby, B.H.1
  • 46
    • 0028746205 scopus 로고
    • A Correction for Powder Diffraction Peak Asymmetry Due to Axial Divergence
    • Finger, L. W.; Cox, D. E.; Jephcoat, A. P. A Correction for Powder Diffraction Peak Asymmetry Due to Axial Divergence J. Appl. Crystallogr. 1994, 27, 892-900
    • (1994) J. Appl. Crystallogr. , vol.27 , pp. 892-900
    • Finger, L.W.1    Cox, D.E.2    Jephcoat, A.P.3
  • 48
    • 34548810358 scopus 로고    scopus 로고
    • Towards Quantitative Analysis of Intermolecular Interactions with Hirshfeld Surfaces
    • Mckinnon, J. J.; Jayatilaka, D.; Spackman, M. A. Towards Quantitative Analysis of Intermolecular Interactions with Hirshfeld Surfaces Chem. Commun. 2007, 3814-3816
    • (2007) Chem. Commun. , pp. 3814-3816
    • McKinnon, J.J.1    Jayatilaka, D.2    Spackman, M.A.3
  • 49
    • 0001553329 scopus 로고
    • Bonded-Atom Fragments for Describing Molecular Charge Densities
    • Hirshfeld, F. L. Bonded-Atom Fragments for Describing Molecular Charge Densities Theoret. Chim. Acta 1977, 44, 129-138
    • (1977) Theoret. Chim. Acta , vol.44 , pp. 129-138
    • Hirshfeld, F.L.1
  • 50
    • 84875827943 scopus 로고    scopus 로고
    • Molecules in Crystals
    • Spackman, M. A. Molecules in Crystals Phys. Scr. 2013, 87, 048103
    • (2013) Phys. Scr. , vol.87 , pp. 048103
    • Spackman, M.A.1
  • 51
    • 0042362575 scopus 로고    scopus 로고
    • Fingerprinting Intermolecular Interactions in Molecular Crystals
    • Spackman, M. A.; Mckinnon, J. J. Fingerprinting Intermolecular Interactions in Molecular Crystals CrystEngComm 2002, 4, 378-392
    • (2002) CrystEngComm , vol.4 , pp. 378-392
    • Spackman, M.A.1    McKinnon, J.J.2
  • 54
    • 33750559983 scopus 로고    scopus 로고
    • Semiempirical GGA-Type Density Functional Constructed with a Long-Range Dispersion Correction
    • Grimme, S. Semiempirical GGA-Type Density Functional Constructed with a Long-Range Dispersion Correction J. Comput. Chem. 2006, 27, 1787-1799
    • (2006) J. Comput. Chem. , vol.27 , pp. 1787-1799
    • Grimme, S.1
  • 55
    • 33747791903 scopus 로고    scopus 로고
    • V6.0; Accelrys Software: San Diego, CA
    • MS Modeling, V6.0; Accelrys Software: San Diego, CA, 2005.
    • (2005) MS Modeling
  • 58
    • 77949520834 scopus 로고    scopus 로고
    • The Spectral Signatures of Frenkel Polarons in H- and J-Aggregates
    • Spano, F. C. The Spectral Signatures of Frenkel Polarons in H- and J-Aggregates Acc. Chem. Res. 2009, 43, 429-439
    • (2009) Acc. Chem. Res. , vol.43 , pp. 429-439
    • Spano, F.C.1
  • 59
    • 0034670844 scopus 로고    scopus 로고
    • Coupled-Cluster Approach for Studying the Electronic and Nonlinear Optical Properties of Conjugated Molecules
    • Shuai, Z.; Brédas, J. L. Coupled-Cluster Approach for Studying the Electronic and Nonlinear Optical Properties of Conjugated Molecules Phys. Rev. B 2000, 62, 15452-15460
    • (2000) Phys. Rev. B , vol.62 , pp. 15452-15460
    • Shuai, Z.1    Brédas, J.L.2
  • 60
    • 84943032324 scopus 로고
    • Electronic Structure and Spectra of Nitrogen Heterocycles
    • Mataga, N.; Nishimoto, K. Electronic Structure and Spectra of Nitrogen Heterocycles Z. Phys. Chem. 1957, 13, 140-157
    • (1957) Z. Phys. Chem. , vol.13 , pp. 140-157
    • Mataga, N.1    Nishimoto, K.2
  • 62
    • 0032495790 scopus 로고    scopus 로고
    • Intramolecular Nonbonded S···O Interaction Recognized in (Acylimino)Thiadiazoline Derivatives as Angiotensin II Receptor Antagonists and Related Compounds
    • Nagao, Y.; Hirata, T.; Goto, S.; Sano, S.; Kakehi, A.; Iizuka, K.; Shiro, M. Intramolecular Nonbonded S···O Interaction Recognized in (Acylimino)Thiadiazoline Derivatives as Angiotensin II Receptor Antagonists and Related Compounds J. Am. Chem. Soc. 1998, 120, 3104-3110
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 3104-3110
    • Nagao, Y.1    Hirata, T.2    Goto, S.3    Sano, S.4    Kakehi, A.5    Iizuka, K.6    Shiro, M.7
  • 63
    • 34247486610 scopus 로고    scopus 로고
    • Comparison of Polymorphic Molecular Crystal Structures through Hirshfeld Surface Analysis
    • Mckinnon, J. J.; Fabbiani, F. P. A.; Spackman, M. A. Comparison of Polymorphic Molecular Crystal Structures through Hirshfeld Surface Analysis Cryst. Growth Des. 2007, 7, 755-769
    • (2007) Cryst. Growth Des. , vol.7 , pp. 755-769
    • McKinnon, J.J.1    Fabbiani, F.P.A.2    Spackman, M.A.3
  • 65
    • 84865239688 scopus 로고    scopus 로고
    • Diketopyrrolopyrrole-Based Semiconducting Polymer Bearing Thermocleavable Side Chains
    • Sun, B.; Hong, W.; Aziz, H.; Li, Y. Diketopyrrolopyrrole-Based Semiconducting Polymer Bearing Thermocleavable Side Chains J. Mater. Chem. 2012, 22, 18950-18955
    • (2012) J. Mater. Chem. , vol.22 , pp. 18950-18955
    • Sun, B.1    Hong, W.2    Aziz, H.3    Li, Y.4
  • 66
    • 84891668036 scopus 로고    scopus 로고
    • Influence of Solubilizing Group Removal Rate on the Morphology and Crystallinity of a Diketopyrrolopyrrole based Compound
    • 10.1021/cg401625p
    • Thankaraj Salammal, S.; Balandier, J.-Y.; Kumar, S.; Goormaghtigh, E.; Geerts, Y. H. Influence of Solubilizing Group Removal Rate on the Morphology and Crystallinity of a Diketopyrrolopyrrole based Compound. Cryst. Growth Des. 2013, 10.1021/cg401625p.
    • (2013) Cryst. Growth Des.
    • Thankaraj Salammal, S.1    Balandier, J.-Y.2    Kumar, S.3    Goormaghtigh, E.4    Geerts, Y.H.5
  • 67
    • 79953882953 scopus 로고    scopus 로고
    • Synthesis and Characterization of Optical and Redox Properties of Bithiophene-Functionalized Diketopyrrolopyrrole Chromophores
    • Burckstummer, H.; Weissenstein, A.; Bialas, D.; Wurthner, F. Synthesis and Characterization of Optical and Redox Properties of Bithiophene- Functionalized Diketopyrrolopyrrole Chromophores J. Org. Chem. 2011, 76, 2426-2432
    • (2011) J. Org. Chem. , vol.76 , pp. 2426-2432
    • Burckstummer, H.1    Weissenstein, A.2    Bialas, D.3    Wurthner, F.4


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