Induced fit interanion discrimination by binding-induced excimer formation
The synthesis, photophysical, and anion-binding properties of a series of di-, tri-, and tetrapodal anion-binding hosts based on aminopyridinium units with pyrenyl reporter groups are described. The ditopic mesitylene-derived calix[4]arene-based host 4 binds strongly to dicarboxylates, particularly...
| Main Authors: | , , , , , , , , , |
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| Format: | Journal Article |
| Published: |
American Chemical Society
2008
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| Online Access: | http://hdl.handle.net/20.500.11937/29442 |
| _version_ | 1848752804714250240 |
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| author | Filby, M. Dickson, S. Zaccheroni, N. Prodi, L. Bonacchi, S. Montalti, M. Paterson, M. Humphries, Terry Chiorboli, C. Steed, J. |
| author_facet | Filby, M. Dickson, S. Zaccheroni, N. Prodi, L. Bonacchi, S. Montalti, M. Paterson, M. Humphries, Terry Chiorboli, C. Steed, J. |
| author_sort | Filby, M. |
| building | Curtin Institutional Repository |
| collection | Online Access |
| description | The synthesis, photophysical, and anion-binding properties of a series of di-, tri-, and tetrapodal anion-binding hosts based on aminopyridinium units with pyrenyl reporter groups are described. The ditopic mesitylene-derived calix[4]arene-based host 4 binds strongly to dicarboxylates, particularly malonate, in a 2:1 anion:host ratio but is essentially nonemissive in the presence of all anions except chloride because of intramolecular quenching by the pyridinium units. Addition of chloride results in a conformational change, giving an initial increase in emission assigned to intramolecular excimer formation. Further chloride addition also results in an increase in the intensity of the pyrenyl monomer emission as chloride binding reduces the acceptor ability of the pyridinium groups. This behavior is not exhibited by control compounds 5 and 6, which lack the ditopic geometry and calixarene spacer unit; however, tripodal 6 forms 1:2 anion:host complexes with a range of anions. © 2008 American Chemical Society. |
| first_indexed | 2025-11-14T08:14:27Z |
| format | Journal Article |
| id | curtin-20.500.11937-29442 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T08:14:27Z |
| publishDate | 2008 |
| publisher | American Chemical Society |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-294422017-09-13T15:27:38Z Induced fit interanion discrimination by binding-induced excimer formation Filby, M. Dickson, S. Zaccheroni, N. Prodi, L. Bonacchi, S. Montalti, M. Paterson, M. Humphries, Terry Chiorboli, C. Steed, J. The synthesis, photophysical, and anion-binding properties of a series of di-, tri-, and tetrapodal anion-binding hosts based on aminopyridinium units with pyrenyl reporter groups are described. The ditopic mesitylene-derived calix[4]arene-based host 4 binds strongly to dicarboxylates, particularly malonate, in a 2:1 anion:host ratio but is essentially nonemissive in the presence of all anions except chloride because of intramolecular quenching by the pyridinium units. Addition of chloride results in a conformational change, giving an initial increase in emission assigned to intramolecular excimer formation. Further chloride addition also results in an increase in the intensity of the pyrenyl monomer emission as chloride binding reduces the acceptor ability of the pyridinium groups. This behavior is not exhibited by control compounds 5 and 6, which lack the ditopic geometry and calixarene spacer unit; however, tripodal 6 forms 1:2 anion:host complexes with a range of anions. © 2008 American Chemical Society. 2008 Journal Article http://hdl.handle.net/20.500.11937/29442 10.1021/ja711012d American Chemical Society restricted |
| spellingShingle | Filby, M. Dickson, S. Zaccheroni, N. Prodi, L. Bonacchi, S. Montalti, M. Paterson, M. Humphries, Terry Chiorboli, C. Steed, J. Induced fit interanion discrimination by binding-induced excimer formation |
| title | Induced fit interanion discrimination by binding-induced excimer formation |
| title_full | Induced fit interanion discrimination by binding-induced excimer formation |
| title_fullStr | Induced fit interanion discrimination by binding-induced excimer formation |
| title_full_unstemmed | Induced fit interanion discrimination by binding-induced excimer formation |
| title_short | Induced fit interanion discrimination by binding-induced excimer formation |
| title_sort | induced fit interanion discrimination by binding-induced excimer formation |
| url | http://hdl.handle.net/20.500.11937/29442 |