Benzoylperylenedicarboximides: Functional dyes with attractive optical and electronic properties

Holtrup, F. O.; Müller, G.; Uebe, Jochen; Müllen, Kläus

doi:10.1016/s0040-4020(97)00381-5

Cited by 17 publications

(6 citation statements)

References 27 publications

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“…N-subtituted 9-bromoperylenimide ( PI–Br ) was synthesized from perylene-3,4,9,10-tetracarboxylic anhydride through monoprotection using 2,6-diisopropylaniline and decarboxylation followed by bromination (Schemes S1–S3, Supporting Information), in accordance with the reported procedure. , The N -(hydroxypropyl)bromonaphthalenimide derivative was converted to the corresponding tributyltin derivative and further subjected to Stille coupling with PI–Br to yield 50% of naphthalenimide–perylenimide conjugate NP (Schemes S1–S3). Model derivatives such as NI–Ac , NI–Ph , PI–Ac , PI–Ph , and T were synthesized according to the reported procedures (see the Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

Energy Transfer in Near-Orthogonally Arranged Chromophores Separated through a Single Bond

et al. 2012

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A combined experimental and theoretical study shows a significant barrier (ca. 100 kJ/mol) to rotation through the interchromophoric carbon−carbon single covalent (1.49 Å) bond between the naphthalenimide and perylenimide units that prevents coplanarization of the two units in the dyad NP, thereby forcing them to act as independent chromophores/redox centers. Upon photoexcitation, highly efficient energy transfer is observed from the naphthalenimide (energy donor) to the perylenimide (energy acceptor) moiety predominantly through Coulombic coupling, completely isolating the orbital overlap (Dexter-type) interaction between the chromophoric units at such short separation by virtue of their orthogonal arrangement. Because Forster's ideal-dipole approximation ignores the contribution from significant higherorder Coulombic interactions at such short distances between donor and acceptor moieties, the complete coupling was computed from the transition densities, giving an estimate of the energy-transfer rate from the naphthalenimide donor to the perylenimide acceptor of k ET = 2.2 × 10 10 s −1 , in agreement with observations. Ultrafast excitation energy (ca. 40 ps, 90%) and electron (<0.5 ps, 10%) transfer from the singlet excited state of naphthalenimide to the perylenimide moiety competes with further delayed processes in the conjugate NP. Upon excitation at 345 nm, conjugate NP exhibits near-quantitative energy transfer in conjunction with solvent-polarity-dependent (solvatochromic) perylenimide fluorescence, resulting in a remarkable Stoke's shift of ca. 175−240 nm. Favorable photophysical properties such as high fluorescence quantum yield, wide excitation range, ultrafast energy transfer, marginal electron transfer, and large Stoke's shift make this conjugate a potential candidate for biological applications.

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Section: Resultsmentioning

confidence: 99%

Energy Transfer in Near-Orthogonally Arranged Chromophores Separated through a Single Bond

et al. 2012

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“…Therefore, it was necessary to modify the conditions as reported elsewhere for derivatives of 1. [20] Successful intermolecular coupling of 3 a and b in almost quantitative yield was achieved by adding a solution of FeCl 3 in nitromethane, rather than solid FeCl 3 , to a solution of the precursors in dichloromethane, while strongly purging with argon. Predissolving the oxidizing agent in nitromethane speeds up the desired reaction, while bubbling with argon helps to remove evolving HCl, which otherwise facilitates undesired chlorination of the aromatic reactant.…”

Section: Resultsmentioning

confidence: 99%

Novel Perylene Chromophores Obtained by a Facile Oxidative Cyclodehydrogenation Route

2001

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New perylene chromophores, phenyl-substituted diindeno[1,2,3-cd:1',2',3'-lm]perylenes 5a,b and 4,4',7,7'-tetraphenyldiacenaphtho[1,2-k:1',2',k']diindeno[1,2,3-cd:1',2',3'-me]perylenes 22a,b, have been synthesized from substituted fluoranthene derivatives 3a,b and 4a,b by means of a surprisingly simple oxidative cyclodehydrogenation reaction. The resulting chromophores, when substituted with alkyl chains at the periphery, show good solubility in organic solvents, and a full characterization of the novel red, green, and blue dyes by field-desorption mass spectrometry, UV/Vis and 1H and 13C NMR spectroscopy becomes possible.

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“…Perylenetetracarboxylic diimides can also function as charge-transfer participants 10e and charge carriers . Both the optical and redox characteristics of these chromophores can be manipulated by varying the substituents on the imide functions. 10b, Substitutions in the bay regions of the perylene core can make these materials even excellent electron donors . Thus, suitable chemical modification can make perylenetetracarboxylic diimide an ideal accessory pigment acting as an electron acceptor to porphyrin chromophores 10e,15 and electron donor to fullerenes.…”

Section: Introductionmentioning

confidence: 99%

[60]Fullerene-Based Molecular Triads with Expanded Absorptions in the Visible Region: Synthesis and Photovoltaic Properties

Xiao

et al. 2004

J. Phys. Chem. B

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Photoactive fulleropyrrolidine-perylenetetracarboxylic diimide-porphyrin triad (FPP) and its zinc analogue (ZnFPP) with expanded absorptions in the visible spectral region were synthesized. Steady absorption spectra and cyclic voltammetry (CV) measurement showed rather weak electronic interactions among the component chromophores in the ground state within the triads. Preliminary fluorescence measurements indicated the occurrence of a photoinduced electron-transfer process within the triads. These processes can be elicited either in the excited state of the perylenetetracarboxylic diimide chromophore or in the excited state of the porphyrin chromophore. The existence of photoinduced charge-separated states within triads in solution was confirmed by steady-state photolysis in the presence of methyl viologen (MV 2+ ) as a sacrificed electron acceptor and 1-benzyl-1,4-dihydronicotinamide (BNAH) as a sacrificed electron donor. The photovoltaic devices have been fabricated on the basis of the triads and have shown clear photovoltaic behavior under illumination of white light. Though the power conversion efficiencies under simulated solar illumination of 68 mW‚cm -2 were found to be moderate (0.028% for FPP and 0.035% for ZnFPP), it is an encouraging result for application of such molecular donor-acceptor ensembles to photovoltaics.

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Benzoylperylenedicarboximides: Functional dyes with attractive optical and electronic properties

Cited by 17 publications

References 27 publications

Energy Transfer in Near-Orthogonally Arranged Chromophores Separated through a Single Bond

Energy Transfer in Near-Orthogonally Arranged Chromophores Separated through a Single Bond

Novel Perylene Chromophores Obtained by a Facile Oxidative Cyclodehydrogenation Route

[60]Fullerene-Based Molecular Triads with Expanded Absorptions in the Visible Region: Synthesis and Photovoltaic Properties

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