19. Die Kristallstruktur der Diphenylpolyene

Hengstenberg, J.; Kühn, Richard

doi:10.1515/zkri-1930-0120

Cited by 15 publications

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“…The cell parameters of the monoclinic crystal of 1 were first reported in 1930. 9 The compound was then found out to crystallize in two polymorphic forms (monoclinic and orthorhombic), and the cell parameters and the space groups of both forms (monoclinic P2 1 /c and orthorhombic Pbca) were determined from Weissenberg photographs. 10 The crystal structure of the orthorhombic form has already been determined at 293 K. 11 Crystal structure of monoclinic form Crystal structure analysis of the monoclinic form was carried out at room temperature and 90 K. An ORTEP drawing of the molecule is shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

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Conformational change of all-trans-1,6-diphenyl-1,3,5-hexatriene in two crystalline forms

2008

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Section: Resultsmentioning

confidence: 99%

“…The unit cell parameters determined at room temperature are comparable with those reported in the literature. 9,10 The molecule lies at a crystallographic inversion center, taking all s-trans conformation.…”

Section: Resultsmentioning

confidence: 99%

Conformational change of all-trans-1,6-diphenyl-1,3,5-hexatriene in two crystalline forms

2008

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“…[30][31][32][33] The corresponding all-trans conformations optimized at the b3ly p/6-31G** level are planar, possess a C 2h symmetry, and are true energy minima as all their vibrational frequencies are positive. Table I lists the most relevant structural parameters for discussing these molecular structures.…”

Section: A On the Ground Electronic Statementioning

confidence: 99%

“…This paper examines the molecular structure of the most stable form in the ground electronic state of ␣,-diphenylpolyenes with 1-7 ethylene bonds, which is the all-trans configuration [30][31][32][33] ͑see Scheme I͒, based on density functional theory ͑DFT͒ calculations involving optimization of the geometry. Electronic transitions were evaluated at the TD level.…”

Section: Introductionmentioning

confidence: 99%

On the inversion of the 1 Bu and 2 Ag electronic states in α,ω-diphenylpolyenes

Catalán

2003

The Journal of Chemical Physics

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An alternative model to that of the inversion of the states 1 Bu and 2 Ag is proposed for interpreting the photophysics of the α,ω-diphenylpolyenes. This model is based upon the existence of two chemical structures with Bu symmetry, which may be ascribed to the same excited electronic state 1 Bu. One of the two chemical structures corresponds to the Franck–Condon structure with conjugated single and double bonds for the polyene chain, and another consists of a nearly equivalent series of partial double bonds along the polyene chain. The latter relaxed structure is consistent with the observation of high torsional energy barriers and low photoisomerization quantum yields for diphenylhexatriene in the singlet excited state manifold. Interestingly, such a simple quantum model as that of the particle in a one-dimensional box provides quite an accurate description of the absorption spectroscopic properties of these major compounds. This is partly the result of the most stable structures for these compounds being of the all-trans type; such structures increase in length as additional ethylene units are added, which makes them very similar to a one-dimensional box becoming increasingly longer.

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“…Thus, in 1930, Hengstenberg and Kuhn [34] analyzed the crystalline structures of a series of α,ω-diphenylpolyenes and concluded that the first four (n = 1-4) crystallize in the monoclinic system and that those with the highest chain (n = 5-7) crystallize in the orthorhombic system. In 1940, Krishnan et al [35,36] showed that diphenyloctatetraene also crystallizes in the orthorhombic system.…”

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Photophysics of the electronic states S₀ and S₁ for the coplanar molecular structures of the α,ω‐diphenylpolyenes DPH and DPO

Catalán

2021

J of Physical Organic Chem

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Spectroscopy of the monoclinic and orthorhombic crystalline forms of alltrans-diphenylhexatriene (DPH) and all-trans-diphenyloctatetraene (DPO)show absorption and emission bands that do not generate the widely known Stokes shift of the polyene compounds, discovered by Hausser et al. in 1953 and repeatedly studied over the last 60 years. It can be concluded from our study that the crystallization system, whether in a monoclinic or orthorhombic system, does not significantly influence the photophysics of DPH and DPO in the crystal phase. K E Y W O R D S absorption and emission spectra of single crystals of DPH and DPO, photophysics of coplanar structures of diphenylpolyenes, Stokes shift of diphenylpolyenes | INTRODUCTIONResearch on the spectroscopy of polyene compounds has grown substantially over the last century for several reasons: (a) the central role played by retinal chromophores in the biochemistry of vision, [1,2] (b) by the role played by carotenoid antennas in the photosynthesis process, [3,4] (c) because β-carotene is the molecular structure of provitamin A, [5] and (d) because the spectral behavior of polyenes was essential both for Lewis [6] to establish the theory of color in organic chemistry and for Maccoll [7] to develop his reasoning about the resonance effect.It is noteworthy to emphasize the importance of these compounds in the construction of volume-conserving models for the mechanism of cis-trans photoisomerization in the bicycle-pedal [8] or hula-twist [9,10] process, which are crucial to understand the photoisomerization of 11-cis-retinal to all-trans-retinal that

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19. Die Kristallstruktur der Diphenylpolyene

Cited by 15 publications

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Conformational change of all-trans-1,6-diphenyl-1,3,5-hexatriene in two crystalline forms

Conformational change of all-trans-1,6-diphenyl-1,3,5-hexatriene in two crystalline forms

On the inversion of the 1 Bu and 2 Ag electronic states in α,ω-diphenylpolyenes

Photophysics of the electronic states S₀ and S₁ for the coplanar molecular structures of the α,ω‐diphenylpolyenes DPH and DPO

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19. Die Kristallstruktur der Diphenylpolyene

Cited by 15 publications

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Conformational change of all-trans-1,6-diphenyl-1,3,5-hexatriene in two crystalline forms

Conformational change of all-trans-1,6-diphenyl-1,3,5-hexatriene in two crystalline forms

On the inversion of the 1 Bu and 2 Ag electronic states in α,ω-diphenylpolyenes

Photophysics of the electronic states S0 and S1 for the coplanar molecular structures of the α,ω‐diphenylpolyenes DPH and DPO

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Photophysics of the electronic states S₀ and S₁ for the coplanar molecular structures of the α,ω‐diphenylpolyenes DPH and DPO