Selective Syntheses and Derivatisation of A2B-Type meso-Triarylcorroles

Eduard Dolusic, Hanna Radecka, Jerzy Radecki, Wim Dehaen

Research output: Contribution to conferencePoster

Abstract

Corroles are porphyrin analogues, lacking one meso carbon. Until recently they were rather rare chemicals, but in the last few years a number of publications have appeared describing the synthesis of corroles and core-modified corroles. This has made these interesting compounds much more available than before, allowing the study of their coordination chemistry, applications of metallocorroles in catalysis and their photophysical behaviour. In this work a two-step synthesis of sterically encumbered triarylcorroles by an acid catalysed condensation of dipyrromethanes and aromatic aldehydes followed by oxidation with p-chloranil (or DDQ) is described. An attempt has been made to optimise the yields by varying the reaction conditions in the syntheses of several model compounds and then extend the use of the optimised conditions for the preparation of more target compounds. Careful monitoring of temperature, solvent, acidic catalyst and reaction time ultimately gave a reliable yield of 15-20% of the corroles, which is a significant improvement as compared to the procedures published earlier. A2B substituted corroles have been used as sensor elements for small molecules in membranes or self-assembled monolayers. The corroles are much more sensitive than the calixpyrroles we investigated earlier. Alternatively, conjugates with indoles can be prepared in order to give rise to novel probes for indole-binding proteins.
Original languageEnglish
PagesBook of Abstracts, XXVIII International Symposium on Macrocyclic Chemistry, Gdan'sk, Poland, 13-18.07.2003, pp. 103-103
Number of pages1
Publication statusPublished - 2003
EventXXVIII International Symposium on Macrocyclic Chemistry - Gdansk, Poland
Duration: 13 Jul 2003 → …

Conference

ConferenceXXVIII International Symposium on Macrocyclic Chemistry
CityGdansk, Poland
Period13/07/03 → …

Fingerprint

Chloranil
Indoles
Porphyrins
Self assembled monolayers
Aldehydes
Catalysis
corrole
Condensation
Carrier Proteins
Carbon
Membranes
Oxidation
Catalysts
Molecules
Acids
Monitoring
Sensors
Temperature
dipyrromethane
indole

Keywords

  • synthesis
  • molecular probe
  • sensor element
  • triarylcorrole

Cite this

Dolusic, E., Radecka, H., Radecki, J., & Dehaen, W. (2003). Selective Syntheses and Derivatisation of A2B-Type meso-Triarylcorroles. Book of Abstracts, XXVIII International Symposium on Macrocyclic Chemistry, Gdan'sk, Poland, 13-18.07.2003, pp. 103-103. Poster session presented at XXVIII International Symposium on Macrocyclic Chemistry, Gdansk, Poland, .
Dolusic, Eduard ; Radecka, Hanna ; Radecki, Jerzy ; Dehaen, Wim. / Selective Syntheses and Derivatisation of A2B-Type meso-Triarylcorroles. Poster session presented at XXVIII International Symposium on Macrocyclic Chemistry, Gdansk, Poland, .1 p.
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abstract = "Corroles are porphyrin analogues, lacking one meso carbon. Until recently they were rather rare chemicals, but in the last few years a number of publications have appeared describing the synthesis of corroles and core-modified corroles. This has made these interesting compounds much more available than before, allowing the study of their coordination chemistry, applications of metallocorroles in catalysis and their photophysical behaviour. In this work a two-step synthesis of sterically encumbered triarylcorroles by an acid catalysed condensation of dipyrromethanes and aromatic aldehydes followed by oxidation with p-chloranil (or DDQ) is described. An attempt has been made to optimise the yields by varying the reaction conditions in the syntheses of several model compounds and then extend the use of the optimised conditions for the preparation of more target compounds. Careful monitoring of temperature, solvent, acidic catalyst and reaction time ultimately gave a reliable yield of 15-20{\%} of the corroles, which is a significant improvement as compared to the procedures published earlier. A2B substituted corroles have been used as sensor elements for small molecules in membranes or self-assembled monolayers. The corroles are much more sensitive than the calixpyrroles we investigated earlier. Alternatively, conjugates with indoles can be prepared in order to give rise to novel probes for indole-binding proteins.",
keywords = "synthesis, molecular probe, sensor element, triarylcorrole",
author = "Eduard Dolusic and Hanna Radecka and Jerzy Radecki and Wim Dehaen",
year = "2003",
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pages = "Book of Abstracts, XXVIII International Symposium on Macrocyclic Chemistry, Gdan'sk, Poland, 13--18.07.2003, pp. 103--103",
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Dolusic, E, Radecka, H, Radecki, J & Dehaen, W 2003, 'Selective Syntheses and Derivatisation of A2B-Type meso-Triarylcorroles', XXVIII International Symposium on Macrocyclic Chemistry, Gdansk, Poland, 13/07/03 pp. Book of Abstracts, XXVIII International Symposium on Macrocyclic Chemistry, Gdan'sk, Poland, 13-18.07.2003, pp. 103-103.

Selective Syntheses and Derivatisation of A2B-Type meso-Triarylcorroles. / Dolusic, Eduard; Radecka, Hanna; Radecki, Jerzy; Dehaen, Wim.

2003. Book of Abstracts, XXVIII International Symposium on Macrocyclic Chemistry, Gdan'sk, Poland, 13-18.07.2003, pp. 103-103 Poster session presented at XXVIII International Symposium on Macrocyclic Chemistry, Gdansk, Poland, .

Research output: Contribution to conferencePoster

TY - CONF

T1 - Selective Syntheses and Derivatisation of A2B-Type meso-Triarylcorroles

AU - Dolusic, Eduard

AU - Radecka, Hanna

AU - Radecki, Jerzy

AU - Dehaen, Wim

PY - 2003

Y1 - 2003

N2 - Corroles are porphyrin analogues, lacking one meso carbon. Until recently they were rather rare chemicals, but in the last few years a number of publications have appeared describing the synthesis of corroles and core-modified corroles. This has made these interesting compounds much more available than before, allowing the study of their coordination chemistry, applications of metallocorroles in catalysis and their photophysical behaviour. In this work a two-step synthesis of sterically encumbered triarylcorroles by an acid catalysed condensation of dipyrromethanes and aromatic aldehydes followed by oxidation with p-chloranil (or DDQ) is described. An attempt has been made to optimise the yields by varying the reaction conditions in the syntheses of several model compounds and then extend the use of the optimised conditions for the preparation of more target compounds. Careful monitoring of temperature, solvent, acidic catalyst and reaction time ultimately gave a reliable yield of 15-20% of the corroles, which is a significant improvement as compared to the procedures published earlier. A2B substituted corroles have been used as sensor elements for small molecules in membranes or self-assembled monolayers. The corroles are much more sensitive than the calixpyrroles we investigated earlier. Alternatively, conjugates with indoles can be prepared in order to give rise to novel probes for indole-binding proteins.

AB - Corroles are porphyrin analogues, lacking one meso carbon. Until recently they were rather rare chemicals, but in the last few years a number of publications have appeared describing the synthesis of corroles and core-modified corroles. This has made these interesting compounds much more available than before, allowing the study of their coordination chemistry, applications of metallocorroles in catalysis and their photophysical behaviour. In this work a two-step synthesis of sterically encumbered triarylcorroles by an acid catalysed condensation of dipyrromethanes and aromatic aldehydes followed by oxidation with p-chloranil (or DDQ) is described. An attempt has been made to optimise the yields by varying the reaction conditions in the syntheses of several model compounds and then extend the use of the optimised conditions for the preparation of more target compounds. Careful monitoring of temperature, solvent, acidic catalyst and reaction time ultimately gave a reliable yield of 15-20% of the corroles, which is a significant improvement as compared to the procedures published earlier. A2B substituted corroles have been used as sensor elements for small molecules in membranes or self-assembled monolayers. The corroles are much more sensitive than the calixpyrroles we investigated earlier. Alternatively, conjugates with indoles can be prepared in order to give rise to novel probes for indole-binding proteins.

KW - synthesis

KW - molecular probe

KW - sensor element

KW - triarylcorrole

M3 - Poster

SP - Book of Abstracts, XXVIII International Symposium on Macrocyclic Chemistry, Gdan'sk, Poland, 13-18.07.2003, pp. 103-103

ER -

Dolusic E, Radecka H, Radecki J, Dehaen W. Selective Syntheses and Derivatisation of A2B-Type meso-Triarylcorroles. 2003. Poster session presented at XXVIII International Symposium on Macrocyclic Chemistry, Gdansk, Poland, .