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Synthesis, structural characterization, and chiroptical properties of planarly and axially chiral boranils

2‐Amino[2.2]paracyclophane reacts with salicylaldehyde or 2‐hydroxyacetophenone to yield imines that then give access to a new series of boranils (8b–d) upon complexation with BF2. These novel boron‐containing compounds display both planar and axial chiralities and were examined experimentally and c...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2023-04, Vol.35 (4), p.227-246
Main Authors: Macé, Aurélie, Hamrouni, Khaoula, Matozzo, Paola, Coehlo, Max, Firlej, Jakub, Aloui, Faouzi, Vanthuyne, Nicolas, Caytan, Elsa, Cordier, Marie, Pieters, Grégory, Srebro‐Hooper, Monika, Berrée, Fabienne, Carboni, Bertrand, Crassous, Jeanne
Format: Article
Language:English
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Summary:2‐Amino[2.2]paracyclophane reacts with salicylaldehyde or 2‐hydroxyacetophenone to yield imines that then give access to a new series of boranils (8b–d) upon complexation with BF2. These novel boron‐containing compounds display both planar and axial chiralities and were examined experimentally and computationally. In particular, their photophysical and chiroptical properties were studied and compared to newly prepared, simpler boranils (9a–d) exhibiting axial chirality only. Less sophisticated chiral architectures were shown to demonstrate overall stronger circularly polarized luminescence (CPL) activity. Novel circularly polarized fluorescent boranil derivatives, displaying planar and/or axial chirality, are described and analyzed in detail.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.23537