Theoretical investigation of the structure and the electron-vibrational dynamics of 9,9′-spirobifluorene

Lukeš, Vladimı́r; Šolc, Roland; Milota, Franz; Sperling, Jaroslaw; Kauffmann, H. F.

doi:10.1016/j.chemphys.2008.02.066

Cited by 19 publications

(7 citation statements)

References 37 publications

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“…4-left. This shift arises from the interactions between the two orthogonally linked fluorene cores on the LPP or IF moieties [27,28,42,43]. Such red shift in UV-Vis spectra (among other properties) has been already stressed in spiro structures, by Johansson and coworkers [28].…”

Section: Optical Propertiesmentioning

confidence: 87%

The synthesis, physicochemical properties and anodic polymerization of a novel ladder pentaphenylene

Cocherel

Poriel²,

Jeannin³

et al. 2009

Dyes and Pigments

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Section: Optical Propertiesmentioning

confidence: 87%

The synthesis, physicochemical properties and anodic polymerization of a novel ladder pentaphenylene

Cocherel

Poriel²,

Jeannin³

et al. 2009

Dyes and Pigments

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“…In recent years Lukeš et al 8, 9 have calculated the geometry of spirobifluorene derivatives using the AM1 model and the absorption and fluorescence spectra using the collective electronic oscillator method 10. For spiro‐linked oligophenylenes they conclude that the single moieties planarize in the excited state, that a CT across the spiro carbon atom is likely, and that optical excitation leads to a confinement of the energy in only one of the two fluorene fragments.…”

Section: Introductionmentioning

confidence: 99%

Photophysical properties of the asymmetrically substituted spirobifluorenes spiro‐DPO and spiro‐MeO‐DPO

Brendel

Dias

Saragi

et al. 2009

Physica Status Solidi (a)

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The photophysical behaviour of the oxadiazolyl (PBD) and diphenylamino (TAD) substituted spirobifluorenes 2′,7′‐bis‐(N,N‐diphenylamino)‐2‐(5‐(4‐tert‐butylphenyl)‐1,3,4‐oxadiazol‐2‐yl)‐9,9′‐spirobifluoren (spiro‐DPO) and 2′,7′‐bis‐(N,N‐diphenylamino)‐2‐(5‐(4‐tert‐butylphenyl)‐1,3,4‐oxadiazol‐2‐yl)‐9,9′‐spirobifluoren (spiro‐MeO‐DPO) has been investigated by temperature‐dependent steady‐state absorption and luminescence spectroscopy and gated measurements. Fluorescence and phosphorescence lifetime measurements, relative quantum yields and dipole moments of the excited states have been determined. Asymmetrically substituted spirobifluorenes exhibit charge‐transfer (CT) emission due to coupling (spiroconjugation) between the fluorene fragments of spirobifluorene. They show a considerable ground‐state dipole moment and exist as equilibrating conformeres. Population of the CT state only occurs after absorption to the locally excited singlet state. The CT fluorescence is dominated by the emission of two equilibrating conformeres with similar dipole moments. At low temperature they planarize in both molecular halves and show strong phosphorescence that is still detectable at room temperature.

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“…As a structural parameter, BLA has been widely used to interpret electronic spectra of various conjugated molecules [65][66][67][68]. The same work also has been calculated by Lukeš et al [69] for SBF. In this work, BLA is defined just for a fluorene unit of molecules:…”

Section: Equilibrium Geometries Between Ground State and Excited Statementioning

confidence: 95%

“…According to Table 2, the k r calculated for FR, SBF, BFD, and BDA are 4.12 9 10 8 , 2.84 9 10 8 , 9.88 9 10 7 , and 7.50 9 10 8 s -1 , respectively. In experiment, a natural radiative lifetime of 10 ns has been measured for FR in CH 2 Cl 2 , that is, the k r of FR is 1 9 10 8 s -1 [69]. Thus, the evaluations of k r employing Einstein spontaneous emission relationship are relatively accurate here.…”

Section: Compoundsmentioning

confidence: 98%

Toward design of high-performance optoelectronic materials: comparative theoretical studies on the photophysical and charge transport properties of fluorene-based compounds

Sun

Geng

et al. 2012

Theor Chem Acc

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As an important building block for optoelectronic applications, various chemical modifications at C9-position of fluorene have been proposed to enhance its performance by suppressing the well-known keto effect. In order to identify different substitution effects on the photophysical and charge transport properties of fluorene, we systematically study the electronic structures and photophysical behaviors of fluorene (FR) and its three dimerized counterparts, namely, 9,9 0 -spirobifluorene (SBF), 9,9 0 -bifluorenylidene (BFD), and bis(biphenyl-2-2-diyl)allene (BDA), by employing density functional theory calculations. The changes in bond length alternation indicate that the geometrical relaxations of the fluorene unit in its dimerized derivatives are smaller than FR compound. This fact was further proved by the nonradiative decay rate estimated of the first excited singlet state for each compound. Meanwhile, the vibration relaxation analyses suggest that the bridge between two fluorene fragments plays an important role in the nonradiative decay process. In addition, the injection abilities were evaluated in terms of the ionization potentials and electron affinities, and the carrier transport properties were discussed in the framework of Marcus theory. We find BFD could be a better ambipolar transport material, and BDA can be used as a high-efficient luminescent building unit with excellent hole transport property.

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Theoretical investigation of the structure and the electron-vibrational dynamics of 9,9′-spirobifluorene

Cited by 19 publications

References 37 publications

The synthesis, physicochemical properties and anodic polymerization of a novel ladder pentaphenylene

The synthesis, physicochemical properties and anodic polymerization of a novel ladder pentaphenylene

Photophysical properties of the asymmetrically substituted spirobifluorenes spiro‐DPO and spiro‐MeO‐DPO

Toward design of high-performance optoelectronic materials: comparative theoretical studies on the photophysical and charge transport properties of fluorene-based compounds

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