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Modular Two‐Step Access to π‐Extended Naphthyridine Systems—Potent Building Blocks for Organic Electronics
Efficient synthetic approaches for the incorporation of nitrogen into polyaromatic compounds (PACs) in different patterns as stabilising moiety for π‐extended systems and modification tool for optoelectronic properties remain a challenge until today. Herein, we developed a new versatile pathway to n...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9299885/ https://www.ncbi.nlm.nih.gov/pubmed/34755928 http://dx.doi.org/10.1002/anie.202114277 |
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author | Stuck, Fabian Dietl, Martin C. Meißner, Maximilian Sebastian, Finn Rudolph, Matthias Rominger, Frank Krämer, Petra Hashmi, A. Stephen K. |
author_facet | Stuck, Fabian Dietl, Martin C. Meißner, Maximilian Sebastian, Finn Rudolph, Matthias Rominger, Frank Krämer, Petra Hashmi, A. Stephen K. |
author_sort | Stuck, Fabian |
collection | PubMed |
description | Efficient synthetic approaches for the incorporation of nitrogen into polyaromatic compounds (PACs) in different patterns as stabilising moiety for π‐extended systems and modification tool for optoelectronic properties remain a challenge until today. Herein, we developed a new versatile pathway to napthyridine‐based PACs as non‐symmetric and regioisomeric pendant to pyrazine‐based PACs. A combination of a gold‐catalysed synthesis of 2‐aminoquinolines and the development of an in situ desulfonation and condensation of these precursors are the key steps of the protocol. The shape and type of attached functional groups of the PACs can be designed in a late stage of the overall synthetic procedure by the chosen anthranile and backbone of the ynamide introduced in the gold‐catalysed step. Single‐crystal X‐ray diffraction and the investigation of electronic properties of the compounds show the influence of the attached substituents. All naphthyridine‐based PACs show halochromic behaviour implying their use as highly sensitive proton sensor in non‐protic solvents. |
format | Online Article Text |
id | pubmed-9299885 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-92998852022-07-21 Modular Two‐Step Access to π‐Extended Naphthyridine Systems—Potent Building Blocks for Organic Electronics Stuck, Fabian Dietl, Martin C. Meißner, Maximilian Sebastian, Finn Rudolph, Matthias Rominger, Frank Krämer, Petra Hashmi, A. Stephen K. Angew Chem Int Ed Engl Research Articles Efficient synthetic approaches for the incorporation of nitrogen into polyaromatic compounds (PACs) in different patterns as stabilising moiety for π‐extended systems and modification tool for optoelectronic properties remain a challenge until today. Herein, we developed a new versatile pathway to napthyridine‐based PACs as non‐symmetric and regioisomeric pendant to pyrazine‐based PACs. A combination of a gold‐catalysed synthesis of 2‐aminoquinolines and the development of an in situ desulfonation and condensation of these precursors are the key steps of the protocol. The shape and type of attached functional groups of the PACs can be designed in a late stage of the overall synthetic procedure by the chosen anthranile and backbone of the ynamide introduced in the gold‐catalysed step. Single‐crystal X‐ray diffraction and the investigation of electronic properties of the compounds show the influence of the attached substituents. All naphthyridine‐based PACs show halochromic behaviour implying their use as highly sensitive proton sensor in non‐protic solvents. John Wiley and Sons Inc. 2021-12-10 2022-01-21 /pmc/articles/PMC9299885/ /pubmed/34755928 http://dx.doi.org/10.1002/anie.202114277 Text en © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
spellingShingle | Research Articles Stuck, Fabian Dietl, Martin C. Meißner, Maximilian Sebastian, Finn Rudolph, Matthias Rominger, Frank Krämer, Petra Hashmi, A. Stephen K. Modular Two‐Step Access to π‐Extended Naphthyridine Systems—Potent Building Blocks for Organic Electronics |
title | Modular Two‐Step Access to π‐Extended Naphthyridine Systems—Potent Building Blocks for Organic Electronics |
title_full | Modular Two‐Step Access to π‐Extended Naphthyridine Systems—Potent Building Blocks for Organic Electronics |
title_fullStr | Modular Two‐Step Access to π‐Extended Naphthyridine Systems—Potent Building Blocks for Organic Electronics |
title_full_unstemmed | Modular Two‐Step Access to π‐Extended Naphthyridine Systems—Potent Building Blocks for Organic Electronics |
title_short | Modular Two‐Step Access to π‐Extended Naphthyridine Systems—Potent Building Blocks for Organic Electronics |
title_sort | modular two‐step access to π‐extended naphthyridine systems—potent building blocks for organic electronics |
topic | Research Articles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9299885/ https://www.ncbi.nlm.nih.gov/pubmed/34755928 http://dx.doi.org/10.1002/anie.202114277 |
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