Proline Enantiomers Discrimination by (L)-Prolinated Porphyrin Derivative Langmuir–Schaefer Films: Proof of Concept for Chiral Sensing Applications
A porphyrin derivative functionalized with the L-enantiomer of proline amino acid was characterized at the air–pure water interface of the Langmuir trough. The porphyrin derivative was dissolved in dichloromethane solution, spread at the air–subphase interface and investigated by acquiring the surfa...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-08-01
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| Series: | Chemosensors |
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| Online Access: | https://www.mdpi.com/2227-9040/10/8/331 |
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| author | Gabriele Giancane Rosanna Pagano Mario Luigi Naitana Gabriele Magna Manuela Stefanelli Donato Monti Roberto Paolesse Simona Bettini Ludovico Valli |
| author_facet | Gabriele Giancane Rosanna Pagano Mario Luigi Naitana Gabriele Magna Manuela Stefanelli Donato Monti Roberto Paolesse Simona Bettini Ludovico Valli |
| author_sort | Gabriele Giancane |
| collection | DOAJ |
| description | A porphyrin derivative functionalized with the L-enantiomer of proline amino acid was characterized at the air–pure water interface of the Langmuir trough. The porphyrin derivative was dissolved in dichloromethane solution, spread at the air–subphase interface and investigated by acquiring the surface pressure vs. area per molecule Langmuir curves. It is worth observing that the behavior of the molecules of the porphyrin derivative floating film was substantially influenced by the presence of L-proline amino acid dissolved in the subphase (10<sup>−5</sup> M); on the contrary, the physical chemical features of the floating molecules were only slightly influenced by the D-proline dissolved in the subphase. Such an interesting chirality-driven selection was preserved when the floating film was transferred onto solid supports by means of the Langmuir–Schaefer method, but it did not emerge when a spin-coating technique was used for the layering of the tetrapyrrolic derivatives. The obtained results represent proof of concept for the realization of active molecular layers for chiral discrimination: porphyrin derivatives, due to their intriguing spectroscopic and supramolecular properties, can be functionalized with the chiral molecule that should be detected. Moreover, the results emphasize the crucial role of the deposition technique on the features of the sensing layers. |
| first_indexed | 2024-03-09T04:35:41Z |
| format | Article |
| id | doaj.art-37965c3fdd7945d38556d6a95a306f65 |
| institution | Directory Open Access Journal |
| issn | 2227-9040 |
| language | English |
| last_indexed | 2024-03-09T04:35:41Z |
| publishDate | 2022-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Chemosensors |
| spelling | doaj.art-37965c3fdd7945d38556d6a95a306f652023-12-03T13:27:52ZengMDPI AGChemosensors2227-90402022-08-0110833110.3390/chemosensors10080331Proline Enantiomers Discrimination by (L)-Prolinated Porphyrin Derivative Langmuir–Schaefer Films: Proof of Concept for Chiral Sensing ApplicationsGabriele Giancane0Rosanna Pagano1Mario Luigi Naitana2Gabriele Magna3Manuela Stefanelli4Donato Monti5Roberto Paolesse6Simona Bettini7Ludovico Valli8Department of Cultural Heritage, Università del Salento, Via D. Birago, 48, I-73100 Lecce, ItalyDepartment of Biological and Environmental Sciences and Technologies, DISTEBA, University of Salento, Via per Arnesano, I-73100 Lecce, ItalyDepartment of Science, Roma Tre University, Viale Guglielmo Marconi 446, I-00146 Rome, ItalyDepartment of Chemical Science and Technologies, University of Rome Tor Vergata, Via della Ricerca Scientifica 1, I-00133 Rome, ItalyDepartment of Chemical Science and Technologies, University of Rome Tor Vergata, Via della Ricerca Scientifica 1, I-00133 Rome, ItalyDepartment of Chemistry, Sapienza University of Rome, Piazzale Aldo Moro 5, I-00185 Rome, ItalyDepartment of Chemical Science and Technologies, University of Rome Tor Vergata, Via della Ricerca Scientifica 1, I-00133 Rome, ItalyDepartment of Biological and Environmental Sciences and Technologies, DISTEBA, University of Salento, Via per Arnesano, I-73100 Lecce, ItalyDepartment of Biological and Environmental Sciences and Technologies, DISTEBA, University of Salento, Via per Arnesano, I-73100 Lecce, ItalyA porphyrin derivative functionalized with the L-enantiomer of proline amino acid was characterized at the air–pure water interface of the Langmuir trough. The porphyrin derivative was dissolved in dichloromethane solution, spread at the air–subphase interface and investigated by acquiring the surface pressure vs. area per molecule Langmuir curves. It is worth observing that the behavior of the molecules of the porphyrin derivative floating film was substantially influenced by the presence of L-proline amino acid dissolved in the subphase (10<sup>−5</sup> M); on the contrary, the physical chemical features of the floating molecules were only slightly influenced by the D-proline dissolved in the subphase. Such an interesting chirality-driven selection was preserved when the floating film was transferred onto solid supports by means of the Langmuir–Schaefer method, but it did not emerge when a spin-coating technique was used for the layering of the tetrapyrrolic derivatives. The obtained results represent proof of concept for the realization of active molecular layers for chiral discrimination: porphyrin derivatives, due to their intriguing spectroscopic and supramolecular properties, can be functionalized with the chiral molecule that should be detected. Moreover, the results emphasize the crucial role of the deposition technique on the features of the sensing layers.https://www.mdpi.com/2227-9040/10/8/331porphyrinsprolineLangmuir–Schaefer techniqueschiralitysupramolecular aggregationchiral discrimination |
| spellingShingle | Gabriele Giancane Rosanna Pagano Mario Luigi Naitana Gabriele Magna Manuela Stefanelli Donato Monti Roberto Paolesse Simona Bettini Ludovico Valli Proline Enantiomers Discrimination by (L)-Prolinated Porphyrin Derivative Langmuir–Schaefer Films: Proof of Concept for Chiral Sensing Applications Chemosensors porphyrins proline Langmuir–Schaefer techniques chirality supramolecular aggregation chiral discrimination |
| title | Proline Enantiomers Discrimination by (L)-Prolinated Porphyrin Derivative Langmuir–Schaefer Films: Proof of Concept for Chiral Sensing Applications |
| title_full | Proline Enantiomers Discrimination by (L)-Prolinated Porphyrin Derivative Langmuir–Schaefer Films: Proof of Concept for Chiral Sensing Applications |
| title_fullStr | Proline Enantiomers Discrimination by (L)-Prolinated Porphyrin Derivative Langmuir–Schaefer Films: Proof of Concept for Chiral Sensing Applications |
| title_full_unstemmed | Proline Enantiomers Discrimination by (L)-Prolinated Porphyrin Derivative Langmuir–Schaefer Films: Proof of Concept for Chiral Sensing Applications |
| title_short | Proline Enantiomers Discrimination by (L)-Prolinated Porphyrin Derivative Langmuir–Schaefer Films: Proof of Concept for Chiral Sensing Applications |
| title_sort | proline enantiomers discrimination by l prolinated porphyrin derivative langmuir schaefer films proof of concept for chiral sensing applications |
| topic | porphyrins proline Langmuir–Schaefer techniques chirality supramolecular aggregation chiral discrimination |
| url | https://www.mdpi.com/2227-9040/10/8/331 |
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