The vibrational spectra of compounds containing the dimethylamino-group. Part II. p-NN-dimethylaminobenzonitrile and the N-methyltoluidines

Gates, Peter N.; Steele, D.; Pearce, Robert A. R.; Radcliffe, K.

doi:10.1039/p29720001607

Cited by 29 publications

(38 citation statements)

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“…16, 37 Since the favored excited-state geometry of the amino nitrogen is also planar, due to the CT-induced radical cation character, ∆Q e will be reduced by N-phenyl substitution. The changes in the amino wagging angle and the electronic nature of the amino nitrogen might affect the C Ph -N stretching, 38 which has a frequency of ca. 1300 cm Ϫ1 .…”

Section: Discussionmentioning

confidence: 99%

“…1300 cm Ϫ1 . 9,10, 38 In addition to the amino group, the introduction of N-phenyl groups might also perturb the structure of the stilbene moiety, particularly the C᎐ ᎐ C bond length and the C e -Ph torsional angle. It is known that the length of the ethylene group increases in the excited state due to the reduction in doublebond character.…”

Section: Discussionmentioning

confidence: 99%

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Origin of the N-methyl and N-phenyl substituent effects on the fluorescence vibronic structures of trans-4-aminostilbene and its derivatives in hexane

Yang

Wang

Hwang

et al. 2003

Photochem Photobiol Sci

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The origin of the N-substituent effect on the room temperature fluorescence vibronic structures of trans-4-aminostilbene (1), its disubstituted derivatives (2 and 3), and the fused-ring analogs (4) in hexane has been investigated. The fluorescence spectra of aminostilbenes 1-4 in hexane are structured and the intensity ratio of the 0,1 vs. the 0,0 band decreases upon N-methyl or N-phenyl substitution, indicating that the N-substituents reduce the displacement in the equilibrium configuration (deltaQe) between the ground and the excited states. Our data are consistent with a planar fluorescing state for 1-4 in hexane. The N-substituents affect the planarity of the ground state structures as well as the conjugation length allowed for exciton resonance, both of which are in accord with the observed progression in fluorescence vibronic structures. According to our analysis, the conformation effect that is associated with the geometry of the amino group appears to play a major role. The corresponding studies on the solvent effect suggest that the fluorescing state of 1-4 in more polar solvents is also a planar charge-transfer state.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Origin of the N-methyl and N-phenyl substituent effects on the fluorescence vibronic structures of trans-4-aminostilbene and its derivatives in hexane

Yang

Wang

Hwang

et al. 2003

Photochem Photobiol Sci

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“…In this work, we found it helpful to compare the Raman spectra of CV and MG to the normal coordinate analysis of N,N-dimethylaminobenzonitrile (DMABN), published in Ref. 11.…”

Section: Methodsmentioning

confidence: 99%

Resonance Raman study of solvent effects on a series of triarylmethane dyes

Lueck

Daniel

McHale

1993

J Raman Spectroscopy

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Resonance Raman spectroscopy was used to address questions concerning the influence of the solvent on the structure and aggregation state of a series of triarylmethane dye, These molecules are of interest owing to the dramatic solvent effects exhibited in their optical absorption spectra, which have recently been interpreted in terms of intermolecular interactions which perturb the D, symmetry of the cationic dyes. Raman spectra of parafuchsin, malachite green, crystal violet and ethyl violet were compared in various solvents, in order to explore changes in the vibrational modes brought about by aggregation (in water), ion-pair formation (in non-polar solvents) and iondipole interactions (in polar solution). In triply amino-substituted dyes, the data point to the possibility that a resonance structure exists having a positive charge on one of the three nitrogens. It is discussed how the resulting reduction in the expected D, symmetry of the cation affects the resonance Raman spectrum.

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“…The ground state structure of the crystalline and gas phase DMABN has been determined by X-ray di †raction analysis11 and microwave spectroscopy,12 respectively. Vibrational spectra and vibrational analysis of the ground state of DMABN have been carried out by Gates et al 13 and Schneider et al14 using empirical and semi-empirical force Ðeld methods, respectively, and gave conÑicting assignments of several bands. In a recent publication, Okamoto et al 15 reported the same analysis based on both empirical and quantum chemical calculations.…”

Section: Introductionmentioning

confidence: 99%

Vibrational studies of ground state 4-dimethylaminobenzonitrile (DMABN) and its ring deuterated isotopomer DMABN-d4

Kwok

Gould

et al. 2001

Phys. Chem. Chem. Phys.

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The vibrational spectra of compounds containing the dimethylamino-group. Part II. p-NN-dimethylaminobenzonitrile and the N-methyltoluidines

Abstract: The i.r. and Raman spectra of p-chlorobenzonitrile and p-NN-dimethylaminobenzonitrile have been recorded in the range 4000-1 0 cm-I. The fundamental vibrational frequencies of these systems have been computed. On the ' r Part 1, A

Cited by 29 publications

References 0 publications

Origin of the N-methyl and N-phenyl substituent effects on the fluorescence vibronic structures of trans-4-aminostilbene and its derivatives in hexane

Origin of the N-methyl and N-phenyl substituent effects on the fluorescence vibronic structures of trans-4-aminostilbene and its derivatives in hexane

Resonance Raman study of solvent effects on a series of triarylmethane dyes

Vibrational studies of ground state 4-dimethylaminobenzonitrile (DMABN) and its ring deuterated isotopomer DMABN-d4

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