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Volumn 12, Issue 35, 2006, Pages 9046-9055

Hydrogen-bonded oligo(p-phenylenevinylene) functionalized with perylene bisimide: Self-assembly and energy transfer

Author keywords

Energy transfer; Oligo(p phenylenevinylene); Perylene bisimides; Scanning tunneling microscopy; Self assembly; Supramolecular chemistry

Indexed keywords

ENERGY TRANSFER; FLUORESCENCE; HYDROGEN BONDS; HYDROPHOBICITY; MOLECULAR STRUCTURE; SCANNING TUNNELING MICROSCOPY; SELF ASSEMBLY; SUPRAMOLECULAR CHEMISTRY;

EID: 33845424041     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600651     Document Type: Article
Times cited : (52)

References (71)
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    • 1H NMR spectroscopy clearly showed the presence of the 1,6- and 1,6,7-regioisomers in the crude reaction mixture. We have discovered that these isomers can be removed in the case of perylene bisimides with two different substitucnts at the N-imide positions. In the literature, perylenes substituted at the bay positions are often prepared along with small amounts of regioisomers, although this is hardly ever mentioned by the authors, see: a) U. Rohr, C. Kohl, K. Müllen, A. van de Craats, J. Warman. J. Mater. Chem. 2001, 11, 1789-1799;
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    • Rohr, U.1    Kohl, C.2    Müllen, K.3    Van De Craats, A.4    Warman, J.5
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    • Since the dielectric constant of 1,2,4-trichlorobenzene [ε = 2.24 (25 °C)] is lower than that of chloroform [ε = 4.81 (20 °C)] we expect a slightly higher dimerization constant in the former solvent.
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    • note
    • -1), which is an upper limit for the dimerization constant of OPV4UT-PERY, a maximum 70 % of the molecules appear as dimers in solution.
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    • note
    • For OPV4UT-PERY, the lattice constants of a 2D unit cell of oblique symmetry were estimated to be a = 2,66±0.05, b = 5.9±0.2nm, and γ = 71 ± 2° by extrapolation. For OPV4UT, these parameters arc a = 1.99±0.05, ft = 5.4±0.2 nm. and γ = 85 ± 3°.
  • 57
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    • note
    • The substitution at the bay area of the PERY unit (two tert-butylphenoxy groups) is different from that in the donor-acceptor-donor (DAD) triads previously investigated (four tert-butylphenoxy groups). However, we do not anticipate big differences in the bias dependence as unsubstituted perylene bisimide units show a bias-dependent behavior identical to that of the DAD triad with four tert-butylphenoxy groups (see ref. [8b]).
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    • note
    • The perylene bisimide emission maximum in dodecane is shifted hypsochromically from that in chloroform whereas excitonic coupling between π-conjugated chromophores should yield a distinct bathochromic luminescence shift. The temperature-dependent data, however, do exhibit a bathochromic shift upon self-assembly. The blue shift observed upon going from chloroform to dodecane may be due to specific environmental or packing parameters.
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    • See ref. [16b] for a simulated model based on quantum-chemical calculations.
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    • note
    • cm = 580 nm with increasing OPV4UT-PERY concentration, which is similar for both systems.
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    • note
    • This is corroborated by the measured Cotton effects (data not shown), which are totally lost for OPV3UT or strongly decrease in intensity for OPV4UT upon addition of OPV4UT-PERY.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.