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Phase transitions and structures of novel pyrenes potentially useful in photovoltaic applications

Show simple item record Leng S. Wex B. Chan L.H. Graham M.J. Jin S. Jing A.J. Jeong K.-U. Van Horn R.M. Sun B. Zhu M. Kaafarani B.R. Cheng S.Z.D.
dc.contributor.editor 2009 2017-10-03T15:45:41Z 2017-10-03T15:45:41Z 2009
dc.identifier 10.1021/jp810653z
dc.identifier.issn 15206106
dc.description.abstract A series of conjugated compounds, 6,7,15,16-tetrakis(alkylthio) quinoxalino[2',3':9,10]phenanthro[4,5-afe-cjphenazine (TQPP-[SCn]4) (n = 6, 8, 10, and 12), which display p-channel characteristics was synthesized. These materials show promise for use in liquid crystalline photovoltaic applications. To determine their applicability, the different phase structures and transitions of these compounds were studied with differential scanning calorimetry (DSC), polarized light microscopy (PLM), wide-angle X-ray diffraction (WAXD), selected area electron diffraction (SAED), and Fourier transform infrared spectroscopy (FT-IR). Using TQPP-[SCi2]4 as a model compound, DSC and ID WAXD results showed that this compound possesses four crystalline, but no liquid crystalline, phases. Based on structural results obtained from 2D WAXD experiments on oriented samples and SAED patterns from single crystals, the unit cell of the lowest temperature TQPP-[SCi2]4 crystalline phase (Ki) was determined to be monoclinic with dimensions of a = 1.87 nm, b = 0.53 nm, c = 3.51 nm, and j3 = 96.2°. With increasing temperature, the K4 phase transformed to other crystalline phases which all were monoclinic with different crystallographic parameters. The arrangement of the TQPP-[SCi2]4 rigid fused rings changed only slightly in these crystalline phases, yet the conformation of the alkyl chains attached to the rigid cores changed significantly at the phase transitions. For the other TQPP-[SCn]4 compounds, only two phase transitions could be identified. It was determined that the transition temperature can be tuned by modifying the attached alkyl chains at the four corners of the rigid fused rings. One-dimensional WAXD studies indicated that the condensed state phase transitions of these compounds were all crystal-crystal transitions. Although single crystals will provide the highest charge carrier mobility, they are very difficult to grow and incur a high cost in production. On the other hand, liquid crystalline phases are preferred for the ease of processing and reasonable performance in change carrier mobility. Therefore, in order to achieve liquid crystalline phases in these compounds, as desired for their application as organic photovoltaic materials, additional modifications to the alkyl chains and their locations are necessary. © 2009 American Chemical Society.
dc.format.extent Pages: (5403-5411)
dc.language English
dc.publisher WASHINGTON
dc.relation.ispartof Publication Name: Journal of Physical Chemistry B; Publication Year: 2009; Volume: 113; no. 16; Pages: (5403-5411);
dc.source Scopus
dc.title Phase transitions and structures of novel pyrenes potentially useful in photovoltaic applications
dc.type Article
dc.contributor.affiliation Leng, S., Institute of Polymer Science and Engineering, Department of Polymer Science, University of Akron, Akron, OH 44325-3909, United States
dc.contributor.affiliation Wex, B., Department of Natural Sciences, Lebanese American University, Byblos, Lebanon
dc.contributor.affiliation Chan, L.H., Department of Applied Materials and Optoelectronic Engineering, National Chi Nan University, Nantou Hsien, 54561, Taiwan
dc.contributor.affiliation Graham, M.J., Institute of Polymer Science and Engineering, Department of Polymer Science, University of Akron, Akron, OH 44325-3909, United States
dc.contributor.affiliation Jin, S., Department of Chemistry, College of Staten Island and Graduate Center of the City University of New York, Staten Island, NY 10314, United States
dc.contributor.affiliation Jing, A.J., Institute of Polymer Science and Engineering, Department of Polymer Science, University of Akron, Akron, OH 44325-3909, United States
dc.contributor.affiliation Jeong, K.-U., School of Advanced Materials Engineering, Chonbuk National University, Jeonju, South Korea
dc.contributor.affiliation Van Horn, R.M., Institute of Polymer Science and Engineering, Department of Polymer Science, University of Akron, Akron, OH 44325-3909, United States
dc.contributor.affiliation Sun, B., State Key Laboratory for Chemical Fibers and Polymer Materials, Donghua University, Shanghai, 201620, China
dc.contributor.affiliation Zhu, M., State Key Laboratory for Chemical Fibers and Polymer Materials, Donghua University, Shanghai, 201620, China
dc.contributor.affiliation Kaafarani, B.R., Department of Chemistry, American University of Beirut, Beirut, Lebanon
dc.contributor.affiliation Cheng, S.Z.D., Institute of Polymer Science and Engineering, Department of Polymer Science, University of Akron, Akron, OH 44325-3909, United States
dc.contributor.authorAddress Kaafarani, B. R.; Department of Chemistry, American University of Beirut, Beirut, Lebanon; email:
dc.contributor.authorCorporate University: American University of Beirut; Faculty: Faculty of Arts and Sciences; Department: Chemistry;
dc.contributor.authorDepartment Chemistry
dc.contributor.faculty Faculty of Arts and Sciences
dc.contributor.authorInitials Leng, SW
dc.contributor.authorInitials Wex, B
dc.contributor.authorInitials Chan, LH
dc.contributor.authorInitials Graham, MJ
dc.contributor.authorInitials Jin, S
dc.contributor.authorInitials Jing, AJ
dc.contributor.authorInitials Jeong, KU
dc.contributor.authorInitials Van Horn, RM
dc.contributor.authorInitials Sun, B
dc.contributor.authorInitials Zhu, MF
dc.contributor.authorInitials Kaafarani, BR
dc.contributor.authorInitials Cheng, SZD
dc.contributor.authorReprintAddress Kaafarani, BR (reprint author), Amer Univ Beirut, Dept Chem, Beirut, Lebanon.
dc.contributor.authorUniversity American University of Beirut
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dc.description.citedCount 17
dc.description.citedTotWOSCount 20
dc.description.citedWOSCount 20
dc.format.extentCount 9
dc.identifier.coden JPCBF
dc.identifier.pubmedID 19368409
dc.identifier.scopusID 65549158813
dc.publisher.address 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
dc.relation.ispartOfISOAbbr J. Phys. Chem. B
dc.relation.ispartOfIssue 16
dc.relation.ispartofPubTitle Journal of Physical Chemistry B
dc.relation.ispartofPubTitleAbbr J Phys Chem B
dc.relation.ispartOfVolume 113
dc.source.ID WOS:000265269100009
dc.type.publication Journal
dc.subject.otherChemCAS Pyrenes
dc.subject.otherIndex Alkyl chain
dc.subject.otherIndex Channel characteristics
dc.subject.otherIndex Condensed state
dc.subject.otherIndex Crystal transition
dc.subject.otherIndex Crystalline phase
dc.subject.otherIndex Crystalline phasis
dc.subject.otherIndex Crystallographic parameters
dc.subject.otherIndex Fused ring
dc.subject.otherIndex High costs
dc.subject.otherIndex Liquid-crystalline
dc.subject.otherIndex Liquid-crystalline phasis
dc.subject.otherIndex Model compound
dc.subject.otherIndex Organic photovoltaic
dc.subject.otherIndex Oriented sample
dc.subject.otherIndex Photovoltaic applications
dc.subject.otherIndex Polarized light microscopy
dc.subject.otherIndex Rigid core
dc.subject.otherIndex Selected area electron diffraction
dc.subject.otherIndex Tetrakis
dc.subject.otherIndex Transition temperature
dc.subject.otherIndex Unit cells
dc.subject.otherIndex Wide-angle x-ray diffraction
dc.subject.otherIndex Alkylation
dc.subject.otherIndex Carrier mobility
dc.subject.otherIndex Crystalline materials
dc.subject.otherIndex Differential scanning calorimetry
dc.subject.otherIndex Diffraction
dc.subject.otherIndex Fourier transform infrared spectroscopy
dc.subject.otherIndex Light
dc.subject.otherIndex Liquids
dc.subject.otherIndex Single crystals
dc.subject.otherIndex Spectroscopic analysis
dc.subject.otherIndex Phase transitions
dc.subject.otherIndex pyrene derivative
dc.subject.otherIndex article
dc.subject.otherIndex chemistry
dc.subject.otherIndex liquid crystal
dc.subject.otherIndex phase transition
dc.subject.otherIndex photochemistry
dc.subject.otherIndex synthesis
dc.subject.otherIndex thermodynamics
dc.subject.otherIndex Liquid Crystals
dc.subject.otherIndex Phase Transition
dc.subject.otherIndex Photochemistry
dc.subject.otherIndex Pyrenes
dc.subject.otherIndex Thermodynamics
dc.subject.otherKeywordPlus ORDERED MESOPHASE STRUCTURES
dc.subject.otherKeywordPlus CRYSTALLINE TPP POLYETHERS
dc.subject.otherKeywordPlus DISCOTIC LIQUID-CRYSTALS
dc.subject.otherKeywordPlus CONJUGATED POLYMERS
dc.subject.otherKeywordPlus CHAIN CONFORMATION
dc.subject.otherKeywordPlus POLY(ESTER IMIDE)S
dc.subject.otherKeywordPlus METHYLENE UNITS
dc.subject.otherKeywordPlus COLUMNAR PHASE
dc.subject.otherKeywordPlus EVEN NUMBERS
dc.subject.otherKeywordPlus SERIES
dc.subject.otherWOS Chemistry, Physical

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