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Julie Febvay Dr. Charles S. Demmer Dr. Pascal Retailleau Dr. Jeanne Crassous Dr. Laura Abella Prof. Jochen Autschbach Dr. Arnaud Voituriez Dr. Angela Marinetti 《Chemistry (Weinheim an der Bergstrasse, Germany)》2019,25(68):15609-15614
Phosphahelicenes with thiophosphinic acid and ester functions have been obtained by the oxidative photocyclisation of olefins bearing both a benzophenanthrene and a benzophosphole unit. When the method has been extended to olefins bearing a partially saturated benzophospholene unit, a divergent regioselectivity of the photocyclisation step has been observed, leading to new helicenes in which the phosphorus function is located on the external rim of the helical backbone. The observed regioselectivity correlates well with the free-valence numbers of the atoms involved in the photocyclisation reaction (DFT calculations). 相似文献
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Dr. Keihann Yavari Dr. Wylliam Delaunay Dr. Nicolas De Rycke Thibault Reynaldo Dr. Paul Aillard Dr. Monika Srebro-Hooper Victoria Y. Chang Dr. Gilles Muller Dr. Denis Tondelier Bernard Geffroy Dr. Arnaud Voituriez Dr. Angela Marinetti Prof. Muriel Hissler Dr. Jeanne Crassous 《Chemistry (Weinheim an der Bergstrasse, Germany)》2019,25(20):5303-5310
Herein, the experimental physicochemical and chiroptical properties of a series of phosphahelicenes are reported, focusing on their UV/Vis absorption, luminescence, electronic circular dichroism, optical rotations, and circularly polarized luminescence. Furthermore, detailed analysis of absorption and ECD spectra performed with the help of quantum-chemical calculations allowed us to highlight general features of these helicenic phosphines. Finally, due to well-suited electrochemical properties and thermal stability, the systems were successfully used as emitters in organic light-emitting diodes. 相似文献
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Keihann Yavari Dr. Pascal Retailleau Dr. Arnaud Voituriez Dr. Angela Marinetti 《Chemistry (Weinheim an der Bergstrasse, Germany)》2013,19(30):9939-9947
The oxidative photocyclization reactions of olefins that contain 1H‐phosphindole or dibenzophosphole substituents have been applied to the synthesis of P/N‐bi‐heterosubstituted dimeric helicenes, as well as of new [6]‐ and [8]phosphahelicenes. In these photocyclization processes, the configuration of the stereogenic phosphorus center dictates the sense of helical chirality. Thus, by starting from enantiomerically pure P‐menthylphosphole‐oxide units, this method affords enantiopure helical compounds. The helical phosphine oxides were characterized by X‐ray diffraction. After reduction of the phosphine‐oxides, the corresponding helical phosphines have been used as ligands in transition‐metal complexes. The X‐ray crystal structure of a gold chloride complex of a [6]helicene is reported. 相似文献
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Paul Aillard Dr. Arnaud Voituriez Davide Dova Dr. Silvia Cauteruccio Prof. Emanuela Licandro Dr. Angela Marinetti 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(39):12373-12376
Enantiomerically pure thiahelicenes displaying a terminal phosphole unit and a stereogenic phosphorus center have been prepared by oxidative photocyclization of a diaryl‐olefin precursor. Starting from one of these phosphathiahelicene oxides, the corresponding trivalent phosphine–AuI complex is obtained with complete diastereoselectivity. It affords a new, excellent precatalyst for the enantioselective cycloisomerization of N‐tethered enynes (up to 96 % ee). 相似文献
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Synthesis of New Phosphahelicene Scaffolds and Development of Gold(I)‐Catalyzed Enantioselective Allenene Cyclizations
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Paul Aillard Dr. Pascal Retailleau Dr. Arnaud Voituriez Dr. Angela Marinetti 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(34):11989-11993
This paper reports on the development of an efficient synthesis of enantiopure phospha[6]helicenes through a [2+2+2] alkyne cyclotrimerization reaction. The corresponding gold complexes proved to be highly efficient both in terms of catalytic activity and enantioselectivity in [2+2] and [4+2] cycloaddition reactions. Furthermore, in the presence of an external nucleophile, such as water or alcohols, the tandem cyclization/addition reactions take place in high yields and excellent diastereo‐ and enantioselectivities. 相似文献
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