Exciton coupling in various substituted aryl-phthalimide bichromophoric systems

Gawroński, Jacek; Kaźmierczak, Franciszek; Gawrońska, K.; Skowronek, Paweł; Waluk, Jacek; Marczyk, Jan

doi:10.1016/0040-4020(96)00795-8

Cited by 14 publications

(9 citation statements)

References 35 publications

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“…Chloro-substituted phthalimides, 19 4,5-dimethoxyphthalimides and 6,7-dimethoxy-2,3-naphthalimides, 20 as well as 2,3-naphthalimides 21 have also been found suitable for application as chromophores in stereochemical studies. Because of the synthetic potential of diimides as building blocks for a variety of materials, we undertook the study of optical properties of chiral aromatic diimides, i.e., their electronic transitions, absorption, and circular dichroism spectra.…”

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confidence: 99%

Chirality of aromatic bis-imides from their circular dichroism spectra

et al. 2000

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It is demonstrated that chirality of molecules composed of 1,2,4,5‐benzenetetracarboxydiimide (pyromellitic diimide) or 1,4,5,8‐naphthalenetetracarboxydiimide units is reflected by their exciton Cotton effects. The analysis is based on the calculated (ZINDO/S) excited states of the model diimide chromophores 1a and 2a. Rotation of the diimide chromophores around the C‐N bond in diimides 3–5 is evaluated from the dynamic 1H NMR data. A comparison of chiroptical properties of bis‐diimides 3–5 with the CD spectra of bis‐imides 6–8 is also presented. Chirality 12:263–268, 2000. © 2000 Wiley‐Liss, Inc.

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confidence: 99%

Chirality of aromatic bis-imides from their circular dichroism spectra

et al. 2000

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“…This compound, which we crystallized and whose solid-state structure was determined by X-ray diffraction analysis ( Fig. 2 ) [ 11 ], has also been described in literature as a yellow compound [ 12 – 13 ]. The color is not the consequence of any impurity and did not vanish after several recrystallizations and, more importantly, was also observed for the methyl ester and the decarboxylation product, the N -phthaloyl tryptamine ( 14 ).…”

Section: Resultsmentioning

confidence: 99%

“…Such interactions also in solution phase would facilitate decay processes from the excited singlet or triplet state. This concept has also been described by Gawronski et al from exciton CD Cotton effects that have been measured for a series of bichromophoric systems based on phthalimide–linker–donor triades [ 12 ]. Concerning the photochemistry of 10 , a remarkable difference to all other phthalimide derivatives occurred: Neither direct excitation nor triplet (acetone, benzophenone) sensitized conditions led to substrate conversion even after prolonged irradiation.…”

Section: Resultsmentioning

confidence: 99%

Photoinduced electron-transfer chemistry of the bielectrophoric N-phthaloyl derivatives of the amino acids tyrosine, histidine and tryptophan

Griesbeck¹,

Neudörfl²,

Kiff³

2011

Beilstein J. Org. Chem.

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SummaryThe photochemistry of phthalimide derivatives of the electron-rich amino acids tyrosine, histidine and tryptophan 8–10 was studied with respect to photoinduced electron-transfer (PET) induced decarboxylation and Norrish II bond cleavage. Whereas exclusive photodecarboxylation of the tyrosine substrate 8 was observed, the histidine compound 9 resulted in a mixture of histamine and preferential Norrish cleavage. The tryptophan derivative 10 is photochemically inert and shows preferential decarboxylation only when induced by intermolecular PET.

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“…N ‐Substituted phthalimides, N ‐alkylphthalimides and N ‐arylphthalimides, are an important class of compounds for biomedical and chemical applications 23–28. In spite of their wide applicability, available procedures for their synthesis are limited.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of N‐butylphthalimide catalyzed by quaternary phosphonium salt‐type triphase catalysts based on cross‐linked polystyrene microspheres

Gao

Wang

et al. 2011

Int J of Chemical Kinetics

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Chloroacylation reactions of cross-linked polystyrene (CPS) microspheres were conducted with two kinds of ω-chloroacyl chlorides, chloroacetyl chloride, and 4-chlorobutyryl chloride as reagent, respectively, and the chloromethylation reaction of CPS microspheres was also performed using 1,4-bis (chloromethoxy) butane as reagent, obtaining three kinds of modified CPS microspheres on which the exchangeable chlorine atoms were introduced. Subsequently, the reactions of these modified microspheres with triphenylphosphine were carried out, respectively, and three kinds of quaternary phosphonium salt (QPS)-type triphase catalysts (TPC) were prepared. These catalysts were used in the N-alkylation reaction of phthalimide, namely the reaction of phthalimide in water phase with 1-bromobutane in organic phase, resulting in N-butylphthalimide. The effects of main reaction conditions on the triphase-transfer catalysis reaction were examined, and the relationship between the structure and catalytic activity for these TPC was investigated. The experimental results indicate that the prepared QPS-type TPC are effective for the N-alkylation reaction of phthalimide carried out between oil phase and water phase. The polarity of the organic solvent and the temperature affect the reaction rate greatly. The result of the reaction in nitrobenzene having the highest polarity among the used several solvents is the best. It will make the reaction to speed up to raise temperature. The chemical structures of the TPC have crucial influences on the catalytic activity of the TPC.

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Exciton coupling in various substituted aryl-phthalimide bichromophoric systems

Cited by 14 publications

References 35 publications

Chirality of aromatic bis-imides from their circular dichroism spectra

Chirality of aromatic bis-imides from their circular dichroism spectra

Photoinduced electron-transfer chemistry of the bielectrophoric N-phthaloyl derivatives of the amino acids tyrosine, histidine and tryptophan

Synthesis of N‐butylphthalimide catalyzed by quaternary phosphonium salt‐type triphase catalysts based on cross‐linked polystyrene microspheres

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