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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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33845400255
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note
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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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55
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33845437369
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note
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-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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56
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33845460481
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note
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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°.
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note
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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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b) M.J. Ahrens, L. E. Sinks, B. Rybtchinski, W. Liu, B. A. Jones, J. M. Giaimo, A. V. Gusev, A. J. Goshe, D. M. Tiede, M. R. Wasielewski, J. Am. Chem. Soc. 2004, 126, 8284-8294.
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Gusev, A.V.7
Goshe, A.J.8
Tiede, D.M.9
Wasielewski, M.R.10
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62
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33845392223
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note
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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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63
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33845399578
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note
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See ref. [16b] for a simulated model based on quantum-chemical calculations.
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Müllen, K.5
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65
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7244254381
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Angew. Chem. Int. Ed. 2004, 43, 5331-5335.
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66
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4444270267
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E. H. A. Beckers, S. C. J. Meskers, A. P. H. J. Schenning, Z. Chen, F. Würthner, R. A. J. Janssen, J. Phys. Chem. A 2004, 108, 6933-6937.
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Beckers, E.H.A.1
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Chen, Z.4
Würthner, F.5
Janssen, R.A.J.6
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67
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33845439279
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note
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cm = 580 nm with increasing OPV4UT-PERY concentration, which is similar for both systems.
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68
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33845424899
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note
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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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69
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20944436897
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F. J. M. Hoeben, L. M. Herz, C. Daniel, P. Jonkheijm, A. P. H. J. Schenning, C. Silva, S. C. J. Meskers, D. Beljonne, R. T. Phillips, R. H. Friend, E. W. Meijer, Angew. Chem. 2004, 116, 2010-2013;
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Hoeben, F.J.M.1
Herz, L.M.2
Daniel, C.3
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Schenning, A.P.H.J.5
Silva, C.6
Meskers, S.C.J.7
Beljonne, D.8
Phillips, R.T.9
Friend, R.H.10
Meijer, E.W.11
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