Conformational equilibriums in trans-1,2-diarylethylenes manifested in their emission spectra. 4. 3-Anthryl and 3-pyrenyl derivatives

Fischer, G.; Fischer, Ernst Otto

doi:10.1021/j150618a008

Cited by 38 publications

(14 citation statements)

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“…The occurrence of the rotamers of trans-diarylethylenes is well documented. [42][43][44][45][46][59][60][61][62][63][64] The rotamers of compounds which exhibit a variation in the fluorescence spectrum with the excitation wavelength should be almost isoenergetic, 63 i.e., they must show a similar steric interaction. One of the two DFSBO rotamers might be stabilized by intramolecular hydrogen bonding, as indicated in Figure 15.…”

Section: + 1dfsbomentioning

confidence: 99%

Photophysical Properties of The DCM and DFSBO Styryl DyesConsequence for Their Laser Properties

Mialocq

Meyer

1989

Laser Chemistry

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The two styryl dyes, 4-dicyanomethylene-2-methyl-6-P-dimethylaminostyryl-4H-pyran (DCM) and 7- dimethylamino-3-(p-formylstyryl)-l, 4-benzoxazin-2-one (DFSBO) exhibit similar solvent-induced shifts of their absorption and emission spectra related to a large intramolecular charge transfer (ICT) in the first singlet excited state. From the Stokes shift values (vA−vF) and a vectorial analysis of their ground state dipole moment (μg= 6.1 D for DCM and 5.8 D for DFSBO), and using the Lippert-Mataga theory, we have estimated the dipole moments of their fluorescent excited states S1 (μe = 26.3 D for DCM and 27.6 D for DFSBO). Intersystem crossing to the triplet state is totally inefficient in DCM but significant in DFSBO. Moreover the absorption of the DFSBO triplet is quite large in the emission band (600–650 nm), which makes of DFSBO a poor laser dye. Although DCM trans-cis photoisomerization can be quite efficient in non polar solvents (chloroform, tetrahydrofuran), DFSBO does not photoisomerize probably due to steric hindrance and to the S1 character which should be more "benzoxazinone" than ethylenic. DFSBO is also shown to exhibit rotamerism.

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Section: + 1dfsbomentioning

confidence: 99%

Photophysical Properties of The DCM and DFSBO Styryl DyesConsequence for Their Laser Properties

Mialocq

Meyer

1989

Laser Chemistry

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“…Absorption (broken lines) and PL (l ex = 410 nm, solid lines) spectra of HPVAnt in solution (2 10 À5 m in toluene, red), as a thin film (on quartz, blue), and as a single crystal (teal) [28]. …”

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confidence: 99%

Maximizing Field‐Effect Mobility and Solid‐State Luminescence in Organic Semiconductors

et al. 2012

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Conductive and emissive: organic transistors made from a simple styrylanthracene derivative have high charge mobility and high luminescence quantum yields. These properties are attributed to the lack of singlet fission, and challenge the idea that the efficient π interactions required for high mobility always lead to quenching of emission. The transistors emit blue electroluminescence and are stable during operation and storage.

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“…The fluorescence spectra of 6-StQx vary with changing excitation wavelength as observed in many 1 ,Zdiarylethylenes (Bartocci et al, 1984;Fischer, 1981;Mazzucato, 1982). When the excitation wavelength is progressively changed from 320 to 360 nm, the fluorescence maximum of 6-StQx changes from 470 to 476nm in ethanol even though the fluorescence spectrum is broad and structureless.…”

Section: Conformational Equilibriummentioning

confidence: 89%

“…In unsymmetrical 1 ,2-diarylethylenes such as trans-2-styrylnaphthalene (2-StN)t, nearly isoenergetic conformers can be obtained by rotation of the aromatic ring around the quasi-single bond between the aromatic group and ethylenic carbon atoms (Fischer, 1980(Fischer, , 1981Fischer and Fischer, 1981;Mazzucato, 1982). Since each of the ground state conformers in equilibrium has its own distinctive absorption characteristics, different excitation wavelengths can lead to different compositions of conformers in the excited state and consequently to wavelength dependent emission behavior.…”

Section: Introductionmentioning

confidence: 99%

PHOTOPHYSICAL PROPERTIES AND CONFORMATIONAL EQUILIBRIUM OF trans‐6‐STYRYLQUINOXALINE

Kim

Shim

1991

Photochem & Photobiology

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The wavelength dependent fluorescence spectra and bi‐exponential fluorescence decays of trans‐6‐styrylquinoxaline (6‐StQx) indicate that two conformers exist in equilibrium in solution. When comparing the conformationally restricted analogues (5Me‐6‐StQx and 7Me‐6‐StQx) with 6‐StQx, the short‐wavelength absorbing conformer of 6‐StQx can be assigned to conformer(A) and the long‐wavelength absorbing component to conformer(B). The temperature effects on the fluorescence lifetime indicate that the short‐lived conformer(A) is the more stable conformer in non‐polar solvents, while the long‐lived conformer(B) is the stable component in polar solvents. The results of semiempir‐ical AMI and CNDO/S CI calculations on both the ground and excited states are consistent with the conclusions drawn from the spectral data.

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Conformational equilibriums in trans-1,2-diarylethylenes manifested in their emission spectra. 4. 3-Anthryl and 3-pyrenyl derivatives

Cited by 38 publications

References 0 publications

Photophysical Properties of The DCM and DFSBO Styryl DyesConsequence for Their Laser Properties

Photophysical Properties of The DCM and DFSBO Styryl DyesConsequence for Their Laser Properties

Maximizing Field‐Effect Mobility and Solid‐State Luminescence in Organic Semiconductors

PHOTOPHYSICAL PROPERTIES AND CONFORMATIONAL EQUILIBRIUM OF trans‐6‐STYRYLQUINOXALINE

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