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Université de Fribourg

Puckering behavior in six new phosphoric triamides containing aliphatic six- and seven-membered ring groups and a database survey of analogous ring-containing structures

Alviri, Banafsheh Vahdani ; Pourayoubi, Mehrdad ; Saneei, Anahid ; Keikha, Mojtaba ; Lee, Arie van der ; Crochet, Aurélien ; Ajees, A. Abdul ; Nečas, Marek ; Fromm, Katharina M. ; Damodaran, Krishnan ; Jenny, Titus A.

In: Tetrahedron, 2018, vol. 74, no. 1, p. 28–41

The influence of a N heteroatom on the ring conformations of six- and seven- membered aliphatic rings in six new C(O)NHP(O)-based phosphoric triamide structures (analysed by X-ray crystallography) is investigated. Additionally the influence of steric and crystal packing effects is also studied by the analysis of Hirshfeld surfaces. The results are compared to analogous structures with three-...

Université de Fribourg

Laterally stretched polycyclic aromatic hydrocarbons: synthesis of dibenzophenanthroheptaphene and tetrabenzotriphenylenopyranthrene derivatives

Alameddine, Bassam ; Anju, Rajamohanan Sobhana ; Shetty, Suchetha ; Baig, Noorullah ; Al-Sagheer, Fakhreia ; Al-Mousawi, Saleh ; Jenny, Titus A.

In: New Journal of Chemistry, 2017, vol. 41, no. 13, p. 6025–6032

Efficient methods for the synthesis of dibenzophenanthroheptaphene (DBPH) and tetrabenzotriphenylenopyranthrene (TBTP) were developed. As a result, a series of unprecedented derivatives of DBPH (1a–c) and TBTP (2a–b) were conventionally obtained from the Scholl cyclodehydrogenation reaction of their respective tribenzopentaphene synthons. An alternative convergent synthesis of DBPH is also...

Université de Fribourg

Tribenzopentaphene derivatives with lateral aromatic groups: the effect of the nature and position of substituents on emission properties

Alameddine, Bassam ; Anju, Rajamohanan Sobhana ; Al-Sagheer, Fakhreia ; Jenny, Titus A.

In: New Journal of Chemistry, 2016, vol. 40, no. 12, p. 10363–10370

Nine new derivatives of the trapezoidal tribenzopentaphene (TBP) polycyclic aromatic hydrocarbon (PAH) were synthesized via the Suzuki–Miyaura palladium catalyzed cross-coupling reaction. The novel TBP derivatives, which bear various rigid and flexible aromatic groups either at their more accessible (R1) or congested (R2) bases, were fully characterized using high resolution mass...

Université de Fribourg

Controlling the lateral aggregation of perfluoroalkylated hexa-peri-hexabenzocoronenes

Aebischer, Olivier F. ; Aebischer, Annina ; Donnio, Bertrand ; Alameddine, Bassam ; Dadras, Massoud ; Güdel, Hans-Ulrich ; Guillon, Daniel ; Jenny, Titus A.

In: Journal of Materials Chemistry, 2007, vol. 17, no. 13, p. 1262-1267

The investigation of two hexa-peri-hexabenzocoronene (HBC) derivatives carrying linear or branched perfluoroalkylated side chains is reported. Polycondensed aromatic hydrocarbons (PAH) such as HBC derivatives are well known to self-organize to form highly ordered monomolecular stacks, which in turn show a concentration- and solvent-dependent lateral aggregation. However, possible...

Université de Fribourg

Self-aggregated perfluoroalkylated hexa-peri-hexabenzocoronene fibers observed by cryo-SEM and fluorescence spectroscopy

Aebischer, Olivier F. ; Aebischer, Annina ; Tondo, Patrick ; Alameddine, Bassam ; Dadras, Massoud ; Güdel, Hans-Ulrich ; Jenny, Titus A.

In: Chemical Communications, 2006, p. 4221 - 4223

The self-assembled architectures in solution of a new HBC derivative bearing perfluoroalkylated side chains were investigated by optical excitation and emission spectroscopy and correlated to cryo-SEM, a new technique in organic chemistry.

Université de Fribourg

Geometry determination of tetrasubstituted stilbenes by proton NMR spectroscopy

Fluxá, Viviana S. ; Jenny, Titus A. ; Bochet, Christian G.

In: Tetrahedron Letters, 2005, vol. 46(2), p. 3793-3795

A simple spectroscopic method was applied to determine the geometry of tetrasubstituted alkenes. The observation of the ⁵J-coupling constants in proton NMR spectra on the ¹³C satellite signals could confirm the previous misassignment of 2,3-diphenylbutene. Hence, the (E)-isomer showed a 1.5 Hz coupling constant, whereas the (Z)-isomer showed a 1.1 Hz coupling constant. Based on this new...