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Modular Synthesis of Organoboron Helically Chiral Compounds: Cutouts from Extended Helices

Two types of helically chiral compounds bearing one and two boron atoms were synthesized by a modular approach. Formation of the helical scaffolds was executed by the introduction of boron to flexible biaryl and triaryl derived from small achiral building blocks. All‐ortho‐fused azabora[7]helicenes...

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Autores principales: Full, Julian, Panchal, Santosh P., Götz, Julian, Krause, Ana‐Maria, Nowak‐Król, Agnieszka
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7898935/
https://www.ncbi.nlm.nih.gov/pubmed/33244880
http://dx.doi.org/10.1002/anie.202014138
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author Full, Julian
Panchal, Santosh P.
Götz, Julian
Krause, Ana‐Maria
Nowak‐Król, Agnieszka
author_facet Full, Julian
Panchal, Santosh P.
Götz, Julian
Krause, Ana‐Maria
Nowak‐Król, Agnieszka
author_sort Full, Julian
collection PubMed
description Two types of helically chiral compounds bearing one and two boron atoms were synthesized by a modular approach. Formation of the helical scaffolds was executed by the introduction of boron to flexible biaryl and triaryl derived from small achiral building blocks. All‐ortho‐fused azabora[7]helicenes feature exceptional configurational stability, blue or green fluorescence with quantum yields (Φ (fl)) of 18–24 % in solution, green or yellow solid‐state emission (Φ (fl) up to 23 %), and strong chiroptical response with large dissymmetry factors of up to 1.12×10(−2). Azabora[9]helicenes consisting of angularly and linearly fused rings are blue emitters exhibiting Φ (fl) of up to 47 % in CH(2)Cl(2) and 25 % in the solid state. As revealed by the DFT calculations, their P–M interconversion pathway is more complex than that of H1. Single‐crystal X‐ray analysis shows clear differences in the packing arrangement of methyl and phenyl derivatives. These molecules are proposed as primary structures of extended helices.
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spelling pubmed-78989352021-03-03 Modular Synthesis of Organoboron Helically Chiral Compounds: Cutouts from Extended Helices Full, Julian Panchal, Santosh P. Götz, Julian Krause, Ana‐Maria Nowak‐Król, Agnieszka Angew Chem Int Ed Engl Research Articles Two types of helically chiral compounds bearing one and two boron atoms were synthesized by a modular approach. Formation of the helical scaffolds was executed by the introduction of boron to flexible biaryl and triaryl derived from small achiral building blocks. All‐ortho‐fused azabora[7]helicenes feature exceptional configurational stability, blue or green fluorescence with quantum yields (Φ (fl)) of 18–24 % in solution, green or yellow solid‐state emission (Φ (fl) up to 23 %), and strong chiroptical response with large dissymmetry factors of up to 1.12×10(−2). Azabora[9]helicenes consisting of angularly and linearly fused rings are blue emitters exhibiting Φ (fl) of up to 47 % in CH(2)Cl(2) and 25 % in the solid state. As revealed by the DFT calculations, their P–M interconversion pathway is more complex than that of H1. Single‐crystal X‐ray analysis shows clear differences in the packing arrangement of methyl and phenyl derivatives. These molecules are proposed as primary structures of extended helices. John Wiley and Sons Inc. 2021-01-26 2021-02-19 /pmc/articles/PMC7898935/ /pubmed/33244880 http://dx.doi.org/10.1002/anie.202014138 Text en © 2020 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Articles
Full, Julian
Panchal, Santosh P.
Götz, Julian
Krause, Ana‐Maria
Nowak‐Król, Agnieszka
Modular Synthesis of Organoboron Helically Chiral Compounds: Cutouts from Extended Helices
title Modular Synthesis of Organoboron Helically Chiral Compounds: Cutouts from Extended Helices
title_full Modular Synthesis of Organoboron Helically Chiral Compounds: Cutouts from Extended Helices
title_fullStr Modular Synthesis of Organoboron Helically Chiral Compounds: Cutouts from Extended Helices
title_full_unstemmed Modular Synthesis of Organoboron Helically Chiral Compounds: Cutouts from Extended Helices
title_short Modular Synthesis of Organoboron Helically Chiral Compounds: Cutouts from Extended Helices
title_sort modular synthesis of organoboron helically chiral compounds: cutouts from extended helices
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7898935/
https://www.ncbi.nlm.nih.gov/pubmed/33244880
http://dx.doi.org/10.1002/anie.202014138
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