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Volumn 15, Issue 46, 2009, Pages 12580-12584

Pentacene-based polycyclic aromatic hydrocarbon dyads with cofacial solid-state π-stacking

Author keywords

Conjugation; Hydrocarbons; Oligomerization; Pi interactions; Semiconductors

Indexed keywords

CANCER RESEARCH; CHARGE-CARRIER MOBILITY; CONJUGATION; ENVIRONMENTAL SCIENCE; MATERIALS CHEMISTRY; NEAREST NEIGHBORS; ORGANIC CHEMISTRY; PENTACENES; PI INTERACTIONS; THEORETICAL CHEMISTRY; THERMAL GRAVIMETRIC ANALYSIS; TRANSFER INTEGRAL; UV/ VIS SPECTROSCOPY;

EID: 71549119811     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902179     Document Type: Article
Times cited : (35)

References (54)
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    • Under an inert atmosphere, thermal decomposition of 6,13-diethynylated pentacenes has been attributed to the Diels-Alder reaction between the alkyne and the pentacene chromophore, while photochemical decomposition leads to [4+4] intermolecular dimerization similar to anthracene. See:a) M. M. Payne, S. A. Odom, S. R. Parkin, J. E. Anthony, Org. Lett. 2004, 6, 3325-3328;
    • (2004) Org. Lett. , vol.6 , pp. 3325-3328
    • Payne, M.M.1    Odom, S.A.2    Parkin, S.R.3    Anthony, J.E.4
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    • b) For a study of substituent-size effects on solid-state packing and electronic influence on stability, see: a) reference [5b,7b, 10e]; B. H. Northrop, K. N. Houk, A. Maliakal, Photochem. Photobiol. Sci. 2008, 7, 1463-1468.
    • (2008) Photochem. Photobiol. Sci. , vol.7 , pp. 1463-1468
    • Northrop, B.H.1    Houk, K.N.2    Maliakal, A.3
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    • See the Supporting Information for spectra and details
    • See the Supporting Information for spectra and details.
  • 41
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    • Fluorescence quantum efficiencies were obtained by a comparison to cresyl violet Perchlorate in methanol, see: S. J. Isak, E. M. Eyring, J. Phys. Chem. 1992, 96, 1738-1742.
    • (1992) J. Phys. Chem. , vol.96 , pp. 1738-1742
    • Isak, S.J.1    Eyring, E.M.2
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    • note
    • -1.
  • 43
    • 71549156653 scopus 로고    scopus 로고
    • -3. b) CCDC-736049 (2b) CCDC-736050 (2c), CCDC-736051 (2d), CCDC-736052 (2f) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
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    • note
    • -3. See also ref. [15b].
  • 45
    • 71549158003 scopus 로고    scopus 로고
    • note
    • -3. See also ref. [15b].
  • 46
    • 71549128160 scopus 로고    scopus 로고
    • note
    • -3. See also ref. [15b]. The disordered isopropyl groups of molecule B were restrained to have the same geometry as that of one of the ordered isopropyl groups of molecule A by use of the SHELXL SAME instruction. Additionally, the Si-C distances of the disordered triisopropylsilyl group were allowed to refine to a common value. Likewise, the C-C distances of the secondary carbon atoms of the minor component were allowed to refine to a common value.
  • 47
    • 71549118022 scopus 로고    scopus 로고
    • note
    • Torsion angles were calculated from the angle between the least squares plane generated from the carbon atoms of each acene.
  • 49
    • 0035805312 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2001, 40, 1732-1736. For a discussion of the polymorphs of pentacene, see:
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 1732-1736
  • 52
    • 71549165255 scopus 로고    scopus 로고
    • note
    • Neighboring molecules are not related by symmetry, and the leastsquares planes of the acenes in molecule A and B are not parallel, thus requiring an alternative method of measuring the interplanar distances. Distances were measured from every individual acene carbon in molecule A to the neighboring least squares plane generated from the carbon atoms of both acenes in molecule B (and vice versa) to obtain the average value reported.
  • 53
    • 71549156047 scopus 로고    scopus 로고
    • note
    • Interplanar distances were calculated from the distance between the least squares plane generated from the carbon atoms of covalently bonded acenes (the pentacene and its covalently bonded PAH moiety).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.