Assignment of electronic spectrum of perylene

Tanizaki, Yoshié; Yoshinaga, Tetsutaro; Hiratsuka, Hiroshi

doi:10.1016/0584-8539(78)80117-2

Cited by 21 publications

(19 citation statements)

References 15 publications

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“…Perylene's lowest-lying singlet excited state, observed in the absorption spectrum at 440 nm (3 ¼ 34 000 M À1 cm À1 in toluene), consists of four vibrational subbands with a 1400 cm À1 interval and is assigned to a symmetry allowed HOMO / LUMO transition. [33][34][35] The y-axispolarized (L b ) S 2 ) S 0 transition at 253 nm (3 ¼ 52 000 M À1 cm À1 in hexane) is energetically well separated from S 1 by 16 800 cm À1 . As the S 1 ) S 0 transition is allowed, emission from S 1 is also (l max (em) ¼ 444 nm in toluene) allowed and, therefore, the intrinsic lifetime (s 0 ) of 5.5 ns is quite short, and uorescence is strong with a quantum yield near unity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, photophysical and electronic properties of tetra-donor- or acceptor-substitutedortho-perylenes displaying four reversible oxidations or reductions

et al. 2019

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Section: Introductionmentioning

confidence: 99%

Synthesis, photophysical and electronic properties of tetra-donor- or acceptor-substitutedortho-perylenes displaying four reversible oxidations or reductions

et al. 2019

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“…At shorter wavelength region, at 253 nm and at 206 nm, single strong structured vibrational band of absorption is observed. The absorption spectrum of perylene doped in PMMA film is found to be identical to one measured in solution (Tanizaki et al 1978), indicating that the PMMA skeleton does not induce tangible interaction to perylene.…”

Section: Resultsmentioning

confidence: 62%

“…Perylene is one of such hydrocarbons. Its spectrum has been so far investigated and analyzed by a number of groups (Davidsson et al 1986, Gómez et al 1997, Renge 1992, Suganuma et al 2011, Tanizaki et al 1978, Timbolmas et al 2017 with different points of view. In our previous study (Ara et al 2006) SF spectroscopy was applied to different concentrations of perylene to unravel the electronic structures and dynamics of perylene in the relaxed fluorescence state.…”

Section: Introductionmentioning

confidence: 99%

Stark Absorption Study of Perylene Doped in a Poly (Methyl Methacrylate) Polymer Film at Different Concentrations

Ara¹,

Ahmed²

2020

J Bangladesh Acad Sci

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In this article, electric field modulated absorption (Stark absorption, SA) study of perylene doped in a poly (methyl methacrylate) (PMMA) polymer film at the concentrations of 1.0 mol%, 2.0 mol% and 3.0 mol% is presented. The field effects on the absorption spectra were found to originate mostly from the Stark shift induced by a change in molecular polarizability between the ground and excited states. The analyses of SA spectra with the aid of Liptay formalism yielded essentially the same magnitude of the average change in molecular polarizability ( ), evaluated for the S0 S1 transition, for all the concentrations. This finding implies that  of perylene molecule doped in a PMMA film does not depend on concentration. Moreover, the yielded positive  for both the preparations implies that SA spectroscopy is an essential technique to probe spectroscopically that perylene possesses larger molecular polarizability in the excited states than in the ground state.

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“…Reference compound 2 features a lowest-energy absorption band strongly reminiscent of the corresponding band of perylene ( Figure 3). In particular, the two bands feature a similar, wellresolved vibrational structure with comparable vibronic spacings, ~1450 and ~1500 cm -1 , for compound 2 and perylene, respectively, attributable to a totally-symmetric 49 breathing type mode 50 of the perylene moiety. In spite of the extremely low solubility of terminally unsubstituted compound 1 in all common solvents, we could measure its absorption and fluorescence excitation spectra in dimethylsulfoxide, and found a band with shape and position very similar to those of the corresponding band of compound 2 (Figure 3).…”

Section: Lowest-energy Bandmentioning

confidence: 90%

Optical and photophysical properties of anisole- and cyanobenzene-substituted perylene diimides

Pagoaga

Mongin

Caselli

et al. 2016

Phys. Chem. Chem. Phys.

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One- and two-photon absorption cross-sections and spectra and the photophysical properties of eight perylenetetracarboxy-3,4:9,10-diimide (PDI) derivatives are reported and analyzed. The investigated compounds are characterized by direct binding of the phenyl rings of the substituents to the bay positions of the perylene core. They have been designed to test the effects of differences in the electronic nature - electron donating (anisole) or accepting (cyanobenzene) - and binding topology (cis or trans, meta or para disubstitution or tetrasubstitution) of the bay substituents on the above optical and photophysical observables. (TD)DFT and Hückel MO calculations have provided theoretical information on the ground-state geometries, the MOs and the electronic spectra of several model compounds. For tetrasubstituted and cis disubstituted derivatives, strong steric interactions in the bay area determined the preferred conformations, with perylene cores distorted near the substituted bay(s) and a 42-44° twisting of the substituent rings relative to the core, quite irrespective of the electronic nature of the substituents. On the other hand, in trans-disubstituted PDI steric hindrance in the bay areas was much weaker and similar in the cyanobenzene and the anisole derivatives. So, the large differences found in the conformational preferences were completely attributable to electronic effects. With electron-accepting cyanobenzene, the substituent rings were found normal to the central planar perylene core, thus enabling the assignment of the moderate spectroscopic effects to inductive interactions. The DFT analysis of the PDI trans-disubstituted with electron-donating anisoles gave quite strongly distorted perylene-core geometries and less twisted (59°) substituent rings. The corresponding increased substituent/core conjugative interactions resulted in new CT allowed electronic transitions and an extremely pronounced solvent-polarity dependence of the emission spectra and intensities. All anisole substituted PDI feature a very fast radiationless decay path in polar solvents, likely related to a relaxation to a charge-separated configuration in the lowest excited-state.

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Assignment of electronic spectrum of perylene

Cited by 21 publications

References 15 publications

Synthesis, photophysical and electronic properties of tetra-donor- or acceptor-substitutedortho-perylenes displaying four reversible oxidations or reductions

Synthesis, photophysical and electronic properties of tetra-donor- or acceptor-substitutedortho-perylenes displaying four reversible oxidations or reductions

Stark Absorption Study of Perylene Doped in a Poly (Methyl Methacrylate) Polymer Film at Different Concentrations

Optical and photophysical properties of anisole- and cyanobenzene-substituted perylene diimides

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