Bioinspired Heterocyclic Partnership in a Cyanine-Type Acidichromic Chromophore
A new red hair-inspired 1,4-benzothiazine-based scaffold is disclosed herein, built upon a modular D-π-A architecture via condensation of the easily accessible 3-phenyl-2<i>H</i>-1,4-benzothiazine with indole-3-carboxaldehyde. The compound was obtained in around 50% yields and was charac...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-08-01
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| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/25/17/3817 |
| _version_ | 1827708156020523008 |
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| author | Maria Laura Alfieri Lucia Panzella Marco d’Ischia Alessandra Napolitano |
| author_facet | Maria Laura Alfieri Lucia Panzella Marco d’Ischia Alessandra Napolitano |
| author_sort | Maria Laura Alfieri |
| collection | DOAJ |
| description | A new red hair-inspired 1,4-benzothiazine-based scaffold is disclosed herein, built upon a modular D-π-A architecture via condensation of the easily accessible 3-phenyl-2<i>H</i>-1,4-benzothiazine with indole-3-carboxaldehyde. The compound was obtained in around 50% yields and was characterized by complete spectroscopic analysis. The new benzothiazine-based cyanine displayed a characteristic reversible acidichromic behavior with a marked bathochromic shift upon acidification. The chromophore resisted at least fifteen hydrochloric acid/sodium hydroxide cycles without appreciable alterations. The expedient and scalable synthetic procedure together with the pH sensitive chromophoric properties would make the new compound an attractive prototype for novel modular chromophore for pH-sensing and other applications. |
| first_indexed | 2024-03-10T17:00:41Z |
| format | Article |
| id | doaj.art-39b48719b1e041269021f1a72ecdab74 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T17:00:41Z |
| publishDate | 2020-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-39b48719b1e041269021f1a72ecdab742023-11-20T10:59:13ZengMDPI AGMolecules1420-30492020-08-012517381710.3390/molecules25173817Bioinspired Heterocyclic Partnership in a Cyanine-Type Acidichromic ChromophoreMaria Laura Alfieri0Lucia Panzella1Marco d’Ischia2Alessandra Napolitano3Department of Chemical Sciences, University of Naples “Federico II”, I-80126 Naples, ItalyDepartment of Chemical Sciences, University of Naples “Federico II”, I-80126 Naples, ItalyDepartment of Chemical Sciences, University of Naples “Federico II”, I-80126 Naples, ItalyDepartment of Chemical Sciences, University of Naples “Federico II”, I-80126 Naples, ItalyA new red hair-inspired 1,4-benzothiazine-based scaffold is disclosed herein, built upon a modular D-π-A architecture via condensation of the easily accessible 3-phenyl-2<i>H</i>-1,4-benzothiazine with indole-3-carboxaldehyde. The compound was obtained in around 50% yields and was characterized by complete spectroscopic analysis. The new benzothiazine-based cyanine displayed a characteristic reversible acidichromic behavior with a marked bathochromic shift upon acidification. The chromophore resisted at least fifteen hydrochloric acid/sodium hydroxide cycles without appreciable alterations. The expedient and scalable synthetic procedure together with the pH sensitive chromophoric properties would make the new compound an attractive prototype for novel modular chromophore for pH-sensing and other applications.https://www.mdpi.com/1420-3049/25/17/3817benzothiazine-based chromophoresheterocyclic aromatic aldehydecyanine dyesacidichromismpH sensors |
| spellingShingle | Maria Laura Alfieri Lucia Panzella Marco d’Ischia Alessandra Napolitano Bioinspired Heterocyclic Partnership in a Cyanine-Type Acidichromic Chromophore Molecules benzothiazine-based chromophores heterocyclic aromatic aldehyde cyanine dyes acidichromism pH sensors |
| title | Bioinspired Heterocyclic Partnership in a Cyanine-Type Acidichromic Chromophore |
| title_full | Bioinspired Heterocyclic Partnership in a Cyanine-Type Acidichromic Chromophore |
| title_fullStr | Bioinspired Heterocyclic Partnership in a Cyanine-Type Acidichromic Chromophore |
| title_full_unstemmed | Bioinspired Heterocyclic Partnership in a Cyanine-Type Acidichromic Chromophore |
| title_short | Bioinspired Heterocyclic Partnership in a Cyanine-Type Acidichromic Chromophore |
| title_sort | bioinspired heterocyclic partnership in a cyanine type acidichromic chromophore |
| topic | benzothiazine-based chromophores heterocyclic aromatic aldehyde cyanine dyes acidichromism pH sensors |
| url | https://www.mdpi.com/1420-3049/25/17/3817 |
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