Theoretical description of solvent effects on fluorescence spectra of bulky charge transfer compound DMA-DMPP

Parusel, Andreas B. J.; Schamschule, Rudolf; Köhler, Gabriele

doi:10.1002/(sici)1096-987x(19981115)19:14<1584::aid-jcc4>3.0.co;2-f

Cited by 13 publications

(12 citation statements)

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“…Group Orientation Adsorption in the dark a It is well known that heterogeneous photocatalytic oxidations can occur through a mechanism involving OH radicals during the first steps. 16 The reactivity of hydroxyl radical was a subject of intensive studies 17 and the correlation between the selectivity of the attack and the nature of the substituent in homogenous reactions was also recently studied with various experimental [18][19][20][21][22] and theoretical 23 methods. It is reported that the rate of addition of the OH radical to the aromatic rings (k = 10 9 -10 10 l mol 21 s 21 ) is very high and this could mean that the attack should be rather unselective.…”

Section: Speciesmentioning

confidence: 99%

Influence of the substituent on selective photocatalytic oxidation of aromatic compounds in aqueous TiO2 suspensions

et al. 2006

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Section: Speciesmentioning

confidence: 99%

Influence of the substituent on selective photocatalytic oxidation of aromatic compounds in aqueous TiO2 suspensions

et al. 2006

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“…The structure of compounds 3 was confirmed by IR, 1 H NMR, 13 C NMR, mass spectroscopy, and formulae confirm by elemental analysis. For example, the 1 H NMR spectrum of 3a showed a singlet at δ 2.81 for methyl protons, two triplets at δ 3.39 and 3.75 corresponding to -CH 2 and -CH 2 Cl protons, respectively, and aromatic protons showed expected chemical shifts and splitting patterns.…”

Section: Resultsmentioning

confidence: 99%

“…The 4-N,N-dimethylaminophenyl derivatives of bis-pyrazolo [3,4-b;4′,3′-e]pyridine (DMA-DMPP) and pyrazolo [3,4-b]quinoline (DMA-DPPQ) (Fig. 1) are further representatives of bulky π-electron donor-acceptor compounds and were recently investigated in some detail both experimentally and semi-empirically (10)(11)(12)(13)(14)(15)(16). It has been shown that pyrazoloquinoline derivatives are efficient blue emitters with absorption in the near-ultraviolet region and with a fluorescence quantum yield near to unity.…”

Section: Introductionmentioning

confidence: 83%

Effect of substituents on absorption and fluorescence properties of pyrazolo[3,4-b]pyrrolo[2,3-d]pyridines

Ghotekar¹,

Kazi²,

Jachak³

et al. 2008

Can. J. Chem.

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A convenient route was successfully developed for the synthesis of novel heterocycles such as pyrazolo [3,4-b]pyrrolo [2,3-d]pyridines (PPP) from pyrazolo [3,4-b]pyridines in good yield. The PPP derivatives synthesized were further studied for their photophysical properties, and it was observed that absorption and emission λ max changed, owing to the substituent effect at 4 positions. These compounds were obtained from highly reactive starting materials, 5-aminopyrazoles and α-acetyl γ-butyrolactone.Résumé : On a mis au point une voie réactionnelle qui permet de réaliser la synthèse de nouveaux hétérocycles, telles les pyrazolo[3,4-b]pyrrolo[2,3-d]pyridines (PPP) à partir de pyrazolo[3,4-b]pyridines, avec de bons rendements. On a soumis les dérivés PPP synthétisés à des études de leurs propriétés photophysiques et on a observé que les valeurs des λmax de leurs absorptions et de leurs émissions varient sous l'effet d'un changement dans la nature des substituants en position 4. On a obtenu ces composés à partir de produits de départ très réactifs, soit les 5-aminopyrazoles et l'α-acé-tyl-γ-butyrolactone.

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“…Their photophysical properties can widely be varied by substitution and electron-donor substituted bis-pyrazolo-pyridines became good examples for compounds with bulky electron donor and acceptor groups. The most important example is DMA-DMPP, 4-(4'-N, N-dimethylamino-phenyl)-3,5-dimethyl-1,7-diphenyl-bis-pyrazolo-[3,4-b;4', 3'-e]-pyridine, which has been investigated experimentally and theoretically [1][2][3][4]. DMA-DMPP fluoresces with large quantum yield in nonpolar solvents.…”

Section: Introductionmentioning

confidence: 99%

“…Semiempirical calculations including solute-solvent interactions assign the CT fluorescence to an excited state in which a weakly bound electron located on the N, N-dimethylanilino moiety is promoted into an excited orbital located on the bis-pyrazolo-pyridine acceptor subunit. This state is found at high energies in the gas phase but is strongly stabilized in a polar environment [3,4]. In protic solvents dual fluorescence is observed and the long-wavelength band can be ascribed to the CT emission [1].…”

Section: Introductionmentioning

confidence: 99%

Fluorescence Properties of An Electron Acceptor Substituted Bis-Pyrazolo-Pyridine Derivative: NO₂-DMPP

Rechthaler¹,

Schamschule²,

Parusel³

et al. 1999

Acta Phys. Pol. A

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The fluorescence properties of 3,5-dimethyl-1,7-diphenyl-4-(4'-nitrophenyl)-bis-pyrazolo- [3,4-b;4', 3'-e]-pyridine (NO 2 -DMPP) and its parent compound 3"5-dimethyl-1,7-diphenyl-bis-pyrazolo-[3"4-b;4', 3"-e]-pyridine (BPP, without the nitrophenyl substituent) were investigated. BPP is a highly fluorescent blue emitter and the fluorescence properties, the emission wavelength, and the fluorescence quantum yield, depend only slightly on solvent. On the contrary, acceptor substituted NO2-DMPP shows dual fluorescence: A long-wavelength component experiences a red-shift with increasing solvent polarity but is efficiently quenched when the polarity exceeds that of solvents like 1,2-dichloroethane or 1-bromopropane. A weak short-wavelength component changes only slightly its position and intensity upon variation of the solvent but its yield increases strongly at low temperatures. The experimental results are discussed in the context of the results of semiempirical calculations which show that fluorescence originates from two closely lying fluorescent states which change their sequence and properties when the polarity of the solvent is varied. A twisted intramolecular charge transfer (TICT) state does most likely not contribute to the emission properties, because of its high energy.PACS numbers: 33.50.Dq, 34.70.+e *The results of this paper were initially presented at

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Theoretical description of solvent effects on fluorescence spectra of bulky charge transfer compound DMA-DMPP

Cited by 13 publications

References 21 publications

Influence of the substituent on selective photocatalytic oxidation of aromatic compounds in aqueous TiO2 suspensions

Influence of the substituent on selective photocatalytic oxidation of aromatic compounds in aqueous TiO2 suspensions

Effect of substituents on absorption and fluorescence properties of pyrazolo[3,4-b]pyrrolo[2,3-d]pyridines

Fluorescence Properties of An Electron Acceptor Substituted Bis-Pyrazolo-Pyridine Derivative: NO₂-DMPP

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Theoretical description of solvent effects on fluorescence spectra of bulky charge transfer compound DMA-DMPP

Cited by 13 publications

References 21 publications

Influence of the substituent on selective photocatalytic oxidation of aromatic compounds in aqueous TiO2 suspensions

Influence of the substituent on selective photocatalytic oxidation of aromatic compounds in aqueous TiO2 suspensions

Effect of substituents on absorption and fluorescence properties of pyrazolo[3,4-b]pyrrolo[2,3-d]pyridines

Fluorescence Properties of An Electron Acceptor Substituted Bis-Pyrazolo-Pyridine Derivative: NO2-DMPP

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Fluorescence Properties of An Electron Acceptor Substituted Bis-Pyrazolo-Pyridine Derivative: NO₂-DMPP