On the Structure of Cross‐Conjugated 2,3‐Diphenylbutadiene

Abstract

The structure of the cross-conjugated compound 2,3-diphenylbutadiene was investigated by single-crystal X-ray diffraction and computational methods. In the crystal structure the central butadiene fragment adopts an s-gauche geometry [-55.6(2)°torsion angle φ around the essential single bond], whereas the styrene moieties are close to planarity. MP2/6-311G* calculations show that the s-gauche conformation represents the global minimum along the φ coordinate, but also revealed the existence of an s-trans local minimum.

Photoinduced charge transport over branched conjugation pathways: donor–acceptor substituted 1,1-diphenylethene and 2,3-diphenylbutadiene

“…Unsubstituted 2,3-diphenylbutadiene was previously found to adopt a somewhat surprising s-gauche conformation in the solid state, with a torsion angle of 55.61 around the butadiene single bond. 37,38 MP2 and DFT calculations supported that this compound possesses an s-gauche minimum, and also revealed the presence of an s-trans minimum, which is somewhat (depending on the calculation method up to 1.47 kcal mol À1 ) higher in energy. 38,39 The structures of DA1 and DA2 were investigated with 6-311G** DFT/B3LYP calculations.…”

“…37,38 MP2 and DFT calculations supported that this compound possesses an s-gauche minimum, and also revealed the presence of an s-trans minimum, which is somewhat (depending on the calculation method up to 1.47 kcal mol À1 ) higher in energy. 38,39 The structures of DA1 and DA2 were investigated with 6-311G** DFT/B3LYP calculations. In the optimized structure of DA1 (E = À481 363.76 kcal mol À1 ), the torsion angles between the double bond and the aniline and cyanophenyl groups amount to 36.91 and 41.31, respectively (Fig.…”

Pseudomerohedrally twinned crystal structure of 2,3-diphenylbuta-1,3-diene

“…Interestingly enough, a similar torsion angle for this compound is found by electron diffraction in the gas phase [reference given by Roth et al (1991)], so that crystal packing effects can be excluded. In fact, quantum chemical calculations indicate that 2,3-diphenylbuta-1,3-diene also has the same conformation in the crystal and in the free molecule (van Walree et al, 2005). Thus, in both cases, the central torsion angle is a molecular rather than a crystal property.…”

Palladium(0)‐Catalyzed Synthesis of Cross‐Conjugated Polymers: Transformation into Linear‐Conjugated Polymers through the Diels–Alder Reaction

“…X-ray diffraction, as reported by van Walree et al, of 2,3-diphenyl-1,3-diene shows s-gauche to be the preferred geometry with a face-to-face arrangement of the phenyl groups in the solid state. [13] The films of P1-P3 do consist mainly of the units in an s-gauche conformation. It has also been reported that multilayered chromophoric groups show large Stokes shift.…”

“…P2 and P3 films also showed large Stokes shifts (see Figures S2 and S3 in the Supporting Information). [13] The films of P1-P3 do consist mainly of the units in an s-gauche conformation. X-ray diffraction, as reported by van Walree et al, of 2,3-diphenyl-1,3-diene shows s-gauche to be the preferred geometry with a face-to-face arrangement of the phenyl groups in the solid state.…”