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Volumn 22, Issue 23, 2010, Pages 6438-6443

N-type organic semiconductors based on π-deficient pentacenequinones: Synthesis, electronic structures, molecular packing, and thin film transistors

Author keywords

[No Author keywords available]

Indexed keywords

C ATOMS; COMPREHENSIVE STUDIES; ELECTRONWITHDRAWING; ENERGY LEVEL; FIELD-EFFECT MOBILITIES; FRONTIER MOLECULAR ORBITALS; LOWEST UNOCCUPIED MOLECULAR ORBITAL; MOLECULAR PACKINGS; N-CHANNEL; N-TYPE ORGANIC SEMICONDUCTOR; ORGANIC SYNTHESIS; OXIDIZING REAGENTS; WEAK HYDROGEN BOND;

EID: 78651321266     PISSN: 08974756     EISSN: 15205002     Source Type: Journal    
DOI: 10.1021/cm102681p     Document Type: Article
Times cited : (99)

References (54)
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    • Murphy, A.R.1    Fréchet, J.2
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    • 64549147598 scopus 로고    scopus 로고
    • For n-type organic semiconductors based on anthraquinone, see
    • For n-type organic semiconductors based on anthraquinone, see: (a) Mamada, M.; Nishida, J.; Tokito, S.; Yamashita, Y. Chem. Commun. 2009, 2177-2179.
    • (2009) Chem. Commun. , pp. 2177-2179
    • Mamada, M.1    Nishida, J.2    Tokito, S.3    Yamashita, Y.4
  • 13
    • 8544228377 scopus 로고    scopus 로고
    • For reviews on n-type organic semiconductors and n-channel organic thin film transistors, see
    • For reviews on n-type organic semiconductors and n-channel organic thin film transistors, see: (a) Newman, C. R.; Frisbie, C. D.; da Silva Filho, D. A.; Brédas, J.-L.; Ewbank, P. C.; Mann, K. R. Chem. Mater. 2004, 16, 4436-4451.
    • (2004) Chem. Mater. , vol.16 , pp. 4436-4451
    • Newman, C.R.1    Frisbie, C.D.2    Da Silva Filho, D.A.3    Brédas, J.-L.4    Ewbank, P.C.5    Mann, K.R.6
  • 21
    • 78651316819 scopus 로고    scopus 로고
    • Ph.D. Dissertation. Columbia University, NewYork
    • Miao, Q. Ph.D. Dissertation. Columbia University, NewYork, 2005.
    • (2005)
    • Miao, Q.1
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    • 78651312686 scopus 로고    scopus 로고
    • The synthesis of this derivative from 4 and its crystal structure will be reported elsewhere
    • The synthesis of this derivative from 4 and its crystal structure will be reported elsewhere.
  • 38
    • 34548749744 scopus 로고    scopus 로고
    • For examples of synthesis of pentacenequinones using this strategy, see
    • For examples of synthesis of pentacenequinones using this strategy, see: (a) Bénard, C. P.; Geng, Z.; Heuft, M. A.; VanCrey, K.; Fallis, A. G. J. Org. Chem. 2007, 72, 7229-7236.
    • (2007) J. Org. Chem. , vol.72 , pp. 7229-7236
    • Bénard, C.P.1    Geng, Z.2    Heuft, M.A.3    VanCrey, K.4    Fallis, A.G.5
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    • Ref 10
    • Ref 10.
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    • The quadruple weak hydrogen bonds are also found in the reported crystal structures of 16,11-triaza-5,12-tetracenequinone derivatives but were not recognized in that report. See
    • The quadruple weak hydrogen bonds are also found in the reported crystal structures of 1,6,11-triaza-5,12-tetracenequinone derivatives but were not recognized in that report. See: Kim, Y.-S.; Park, S.-Y.; Lee, H.-J.; Suh, M.-E.; Schollmeyer, D.; Lee, C.-O. Bioorg. Med. Chem. 2003, 11, 1709-1714.
    • (2003) Bioorg. Med. Chem. , vol.11 , pp. 1709-1714
    • Kim, Y.-S.1    Park, S.-Y.2    Lee, H.-J.3    Suh, M.-E.4    Schollmeyer, D.5    Lee, C.-O.6
  • 52
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    • The X-ray diffraction patterns of 3 are shown in the Supporting Information and those of 5 were reported in ref 5
    • The X-ray diffraction patterns of 3 are shown in the Supporting Information and those of 5 were reported in ref 5.
  • 53
    • 78651331888 scopus 로고    scopus 로고
    • XRDfrom the film of 3 shows three peaks at 2θ=9.10° (d-spacing: 9.71 Å ), 2θ = 18.49° (d-spacing: 4.80 Å ), and 2θ = 21.67° (d-spacing: 4.10 Å ). In comparison, the first diffraction (002) derived from the single crystal structure of 3 appears at 2θ=12.10° (d-spacing: 7.31 Å ).
    • XRDfrom the film of 3 shows three peaks at 2θ=9.10° (d-spacing: 9.71 Å ), 2θ = 18.49° (d-spacing: 4.80 Å ), and 2θ = 21.67° (d-spacing: 4.10 Å ). In comparison, the first diffraction (002) derived from the single crystal structure of 3 appears at 2θ= 12.10° (d-spacing: 7.31 Å ).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.