N,N′-Bis[2-(4-pyridyl)ethyl]perylene-3,4:9,10-bis(dicarboximide)m-cresol disolvate

Hino, Kazuyuki; Mizuguchi, Jin

doi:10.1107/s1600536805004447

Cited by 7 publications

(4 citation statements)

References 3 publications

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“…The dimers are arranged in two perpendicular layers with the perylene plane of 3a being either perpendicular to the a -axis (dimer B 2 ) or the c -axis (dimer A 2 ) of the unit cell (Figure b). The closest distance between the molecules was determined to 3.27 Å for dimer B 2 whereas for both π-dimers the mean distance between two perylene bisimide π-surfaces was elucidated to 3.47 Å (see Figure S4 in the Supporting Information), which matches well with the distance observed in the solid state for the π–π interactions (3.34–3.55 Å) of the fully planar core-unsubstituted PBIs . Both dimers A 2 and B 2 are characterized by a rotational offset of 43° and 58°, respectively.…”

Section: Resultssupporting

confidence: 72%

Impact of Molecular Flexibility on Binding Strength and Self-Sorting of Chiral π-Surfaces

et al. 2011

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In this work, we have explored for the first time the influence of conformational flexibility of π-core on chiral self-sorting properties of perylene bisimides (PBIs) that are currently one of the most prominent classes of functional dyes. For this purpose, two series of chiral macrocyclic PBIs 3a-c and 4a-c comprising oligoethylene glycol bridges of different lengths at the 1,7 bay positions were synthesized and their atropo-enantiomers (P and M enantiomers) were resolved. Single crystal analysis of atropo-enantiomerically pure (P)-3a not only confirmed the structural integrity of the ethylene glycol bridged macrocycle but also illustrated the formation of π-stacked dimers with left-handed supramolecular helicity. Our detailed studies with the series of highly soluble chiral PBIs 4a-c by 1- and 2-D (1)H NMR techniques, and temperature- and concentration-dependent UV/vis absorption and circular dichroism (CD) spectroscopy revealed that in π-π-stacking dimerization of these PBIs chiral self-recognition (i.e., PP and MM homodimer formation) prevails over self-discrimination (i.e., PM heterodimer formation). Our studies clearly showed that with increasing conformational flexibility of PBI cores imparted by longer bridging units, the binding strength for the dimerization process increases, however, the efficiency for chiral self-recognition decreases. These results are rationalized in terms of an induced-fit mechanism facilitating more planarized π-scaffolds of PBIs containing longer bridging units upon π-π-stacking.

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Section: Resultssupporting

confidence: 72%

Impact of Molecular Flexibility on Binding Strength and Self-Sorting of Chiral π-Surfaces

et al. 2011

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“…Parameter r * depends on the geometry of the system under consideration and can be calculated according to eq 5 by applying standard C(sp 2 )-X bond lengths a and bond angles, as well as the van der Waals radius r vdW of the substituents . In the present case, the bond lengths and angles were taken from single-crystal X-ray data of the planar parent unsubstituted PBI, which yields a value d ( X , X ) = 2.862 Å − a (for details, see the Supporting Information) . The ∑ r * values of the investigated tetrasubstituted perylene bisimides 1 , 2 , 4 , and 5 are collected in Figure (table).…”

Section: Resultsmentioning

confidence: 99%

Effects of Bay Substituents on the Racemization Barriers of Perylene Bisimides: Resolution of Atropo-Enantiomers

2007

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The activation parameters for the interconversion of atropisomers (P- and M-enantiomer) of core-twisted perylene bisimides have been determined by dynamic NMR spectroscopy (DNMR) and time- and temperature-dependent CD spectroscopy. By comparing the activation parameters of a series of perylene bisimides containing halogen or aryloxy substituents in the bay area (1,6,7,12-positions), a clear structure-property relationship has been found that demonstrates that the kinetic and thermodynamic parameters for the inversion of enantiomers are dependent on the apparent overlap parameter Sigmar* of the bay substituents. This study reveals a high stability (DeltaG(368 K) = 118 kJ/mol) for the atropo-enantiomers of tetrabromo-substituted perylene bisimide in solution. Accordingly, the enantiomers of this derivative could be resolved by HPLC on a chiral column. These enantiomers do not racemize in solution at room temperature and, thus, represent the first examples of enantiomerically pure core-twisted perylene bisimides.

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“…PBIs are widely used as pigments and dyes, with colors ranging from red to black depending on the particle size and crystal packing of the dye molecules. [21][22][23][24] In addition to optical features such as strong absorption in the visible region, high quantum yields and excellent photostability, PBIs also display low reduction potentials, 25 which enables their use as electron-acceptors and n-type semiconductors in photoinduced charge-transfer reactions. For these appealing properties, perylene derivatives have been extensively studied for the fabrication of field-effect transistors, 26 luminescent solar concentrators, 27 dye lasers, 28 photovoltaic cells 29 and organic light-emitting diodes (OLEDs).…”

Section: Introductionmentioning

confidence: 99%

MWCNT/perylene bisimide water dispersions for miniaturized temperature sensors

et al. 2015

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N,N′-Bis[2-(4-pyridyl)ethyl]perylene-3,4:9,10-bis(dicarboximide)m-cresol disolvate

Cited by 7 publications

References 3 publications

Impact of Molecular Flexibility on Binding Strength and Self-Sorting of Chiral π-Surfaces

Impact of Molecular Flexibility on Binding Strength and Self-Sorting of Chiral π-Surfaces

Effects of Bay Substituents on the Racemization Barriers of Perylene Bisimides: Resolution of Atropo-Enantiomers

MWCNT/perylene bisimide water dispersions for miniaturized temperature sensors

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