Literature DB >> 20235590

Boron asymmetry in a BODIPY derivative.

Alexandre Haefele1, Chantal Zedde, Pascal Retailleau, Gilles Ulrich, Raymond Ziessel.   

Abstract

A boradiazaindacene (BODIPY) fluorophore with a chirality held on the central boron has been synthesized and the racemate resolved. Dissymetrization of the BODIPY core was obtained by oxidation of the 3-methyl group to the corresponding carboxaldehyde. A hydrogen bond between the aldehyde proton and the fluorine on the boron atom was evidenced by both (1)H NMR and X-ray diffraction. Chiral high-performance liquid chromatography as well as circular dichroism confirm the persistence of both enantiomers.

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Year:  2010        PMID： 20235590     DOI： 10.1021/ol100109j

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  7 in total

1.  Proton Induced Modulation of ICT and PET Processes in an Imidazo-phenanthroline Based BODIPY Fluorophores.

Authors:  Shrikant S Thakare; Goutam Chakraborty; Shantaram Kothavale; Soumyaditya Mula; Alok K Ray; Nagaiyan Sekar
Journal:  J Fluoresc       Date:  2017-09-06       Impact factor: 2.217

2.  Synthesis of 3,8-dichloro-6-ethyl-1,2,5,7-tetramethyl-BODIPY from an asymmetric dipyrroketone and reactivity studies at the 3,5,8-positions.

Authors:  Ning Zhao; M Graça H Vicente; Frank R Fronczek; Kevin M Smith
Journal:  Chemistry       Date:  2015-03-11       Impact factor: 5.236

3.  Bis(haloBODIPYs) with Labile Helicity: Valuable Simple Organic Molecules That Enable Circularly Polarized Luminescence.

Authors:  César Ray; Esther M Sánchez-Carnerero; Florencio Moreno; Beatriz L Maroto; Antonia R Agarrabeitia; María J Ortiz; Íñigo López-Arbeloa; Jorge Bañuelos; Komlan D Cohovi; Jamie L Lunkley; Gilles Muller; Santiago de la Moya
Journal:  Chemistry       Date:  2016-05-12       Impact factor: 5.236

4.  Stereogenic boron in 2-amino-1,1-diphenylethanol-based boronate-imine and amine complexes.

Authors:  Sebastian Schlecht; Walter Frank; Manfred Braun
Journal:  Beilstein J Org Chem       Date:  2011-05-16       Impact factor: 2.883

5.  Construction of boron-stereogenic compounds via enantioselective Cu-catalyzed desymmetric B-H bond insertion reaction.

Authors:  Guan Zhang; Zhihan Zhang; Mengyuan Hou; Xinping Cai; Kai Yang; Peiyuan Yu; Qiuling Song
Journal:  Nat Commun       Date:  2022-05-12       Impact factor: 17.694

6.  Circularly polarized luminescence by visible-light absorption in a chiral O-BODIPY dye: unprecedented design of CPL organic molecules from achiral chromophores.

Authors:  Esther M Sánchez-Carnerero; Florencio Moreno; Beatriz L Maroto; Antonia R Agarrabeitia; María J Ortiz; Bryan G Vo; Gilles Muller; Santiago de la Moya
Journal:  J Am Chem Soc       Date:  2014-02-21       Impact factor: 15.419

7.  Circularly Polarized Luminescence from Helically Chiral N,N,O,O-Boron-Chelated Dipyrromethenes.

Authors:  Rua B Alnoman; Sandra Rihn; Daniel C O'Connor; Fiona A Black; Bernard Costello; Paul G Waddell; William Clegg; Robert D Peacock; Wouter Herrebout; Julian G Knight; Michael J Hall
Journal:  Chemistry       Date:  2015-11-30       Impact factor: 5.236
  7 in total

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