Determination of the surface acidity of a free-base corrole in a self-assembled monolayer

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 71, Issue 3-4, 2011, Pages 499-505

  Nulens, Wienand ^a   Grabowska, Iwona ^a   Ngo, Thien Huynh ^b   Maes, Wouter ^b,c   Dehaen, Wim ^b   Radecka, Hanna ^a   Radecki, Jerzy ^a  

^a INSTITUTE OF ANIMAL REPRODUCTION AND FOOD RESEARCH   (Poland)

^b UNIVERSITY OF LEUVEN   (Belgium)

^c HASSELT UNIVERSITY   (Belgium)

Author keywords

Corrole; Electrochemical titration; Mixed self assembled monolayer; Osteryoung square wave voltammetry; Surface pK a

Indexed keywords

EID: 84856280361     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-010-9889-y     Document Type: Article

References (41)

1. Z Gross HB Gray 2006 How do corroles stabilize high-valent metals? Comment Inorg. Chem. 27 61 72 10.1080/02603590600666256 10.1080/ 02603590600666256 1:CAS:528:DC%2BD28XntVCns7k%3D
2. Z Gross N Galili I Saltsman 1999 The first direct synthesis of corroles from pyrrole Angew. Chem. Int. Ed. 38 1427 1429 10.1002/(SICI)1521- 3773(19990517)38:10<1427::AID-ANIE1427>3.0.CO;2-1 1:CAS:528: DyaK1MXjsVyksL8%3D
3. Paolesse, R.; Januiqod, L.; Nurco, D.J.; Mini, S.; Sagone, F.; Boschi, T.; Smith, K.M.: 5,10,15-Triphenylcorrole: a product from a modified Rothemund reaction. Chem. Commun. 1307-1308 (1999). doi: 10.1039/a903247i
4. Z Gross HB Gray 2004 Oxidations catalyzed by metallo-corroles Adv. Synth. Catal. 346 165 170 10.1002/adsc.200303145 10.1002/adsc.200303145 1:CAS:528:DC%2BD2cXjt1ensbw%3D
5. AE Meier-Callahan AJ DiBilio L Simkhovich A Mahammad I Goldberg HB Gray Z Gross 2001 Chromium corroles in four oxidation states Inorg. Chem. 40 6788 6793 10.1021/ic010723z 10.1021/ic010723z 1:CAS:528:DC%2BD3MXosVWjt7w%3D
6. A Mahammad HB Gray AE Meier-Callahan Z Gross 2003 Aerobic oxidations catalyzed by chromium corroles J. Am. Chem. Soc. 125 1162 1163 10.1021/.ja028216j 10.1021/ja028216j
7. Collman, J.P.; Kaplum, M.; Decréau, R.A.: Metal corroles as electrocatalysts for oxygen reduction. Dalton Trans. 554-559 (2006). doi: 10.1039/b512982f
8. I Aviv Z Gross 2008 Iron(III) corroles and porphyrins as superior catalysts for the reactions of diazoacetates with nitrogen- or sulfur-containing nucleophilic substrates: synthetic uses and mechanistic insights Chem. Eur. J. 14 3995 4005 10.1002/chem.200701885 10.1002/chem.200701885 1:CAS:528: DC%2BD1cXmtVyqu7c%3D
9. L Simkhovich Z Gross 2001 Iron(IV) corroles are potent catalysts for aziridination of olefins by chloramine-T Tetrahedron Lett. 42 8089 8092 10.1016/S0040-4039(01)01717-8 10.1016/S0040-4039(01)01717-8 1:CAS:528: DC%2BD3MXnsl2qtLg%3D
10. J-M Barbe G Canard S Brandès R Guilard 2005 Organic-inorganic hybrid sol-gel materials incorporating functionalized cobalt(III) corroles for the selective detection of CO Angew. Chem. Int. Ed. 117 3163 3166 10.1002/ange.200463009 10.1002/ange.200463009
11. J Radecki I Stenka E Dolusic W Dehaen J Plavec 2004 Potentiometric discrimination of neutral forms of nitrophenol isomers by liquid membrane isomers incorporated with corroles Comb. Chem. High-throughput Screen. 7 375 381 1:CAS:528:DC%2BD2cXlsFWnsLw%3D
12. J Radecki I Stenka E Dolusic W Dehaen 2006 Corroles as receptors in liquid membrane electrodes and their potentiometric response towards salicylic acid Electrochim. Acta 51 2282 2288 10.1016/j.electacta.2005.02.152 10.1016/j.electacta.2005.02.152 1:CAS:528:DC%2BD28Xht1Gisbw%3D
13. X-B Zhang Z-X Han Z-H Fang G-L Shen R-Q Yu 2006 5,10,15- Tris(pentafluorophenyl)corrole as highly selec-tive neutral carrier for a silver ion-sensitive electrode Anal. Chim. Acta 562 210 215 10.1016/j.aca.2006.01.056 10.1016/j.aca.2006.01.056 1:CAS:528:DC%2BD28XislCgtr0%3D
14. C-H He F-L Ren X-B Zhang Z-X Han 2006 A fluorescent chemical sensor for Hg(II) based on a corrole derivative in a PVC matrix Talanta 70 364 369 10.1016/j.talanta.2006.02.051 10.1016/j.talanta.2006.02.051 1:CAS:528: DC%2BD28XotlWgsLc%3D
15. 2 solar cells J. Porphyr. Phthalocyanines 10 1259 1262 10.1142/S1088424606000624 1:CAS:528: DC%2BD2sXisVyju7k%3D
16. H Agadjanian J Ma A Rentsendorj V Valluripalli JY Hwang A Mahammad DL Farkas HB Gray Z Gross LK Medina-Kauwe 2009 Tumor detection and elimination by a targeted gallium corrole Proc. Natl. Acad. Sci. USA 106 6105 6110 10.1073/pnas.0901531106 10.1073/pnas.0901531106 1:CAS:528:DC%2BD1MXlsFCrtr4%3D
17. I Aviv-Harel Z Gross 2009 Aura of corroles Chem. Eur. J. 15 8382 8394 10.1002/chem.200900920 10.1002/chem.200900920 1:CAS:528:DC%2BD1MXhtVGkurnN
18. Aviv, I.; Gross, Z.: Corrole-based applications. Chem. Commun. 1987-1999 (2007). doi: 10.1039/b618482k
19. I Szymańska M Stobiecka C Orlewska T Rohand D Janssen W Dehaen H Radecka 2008 Electroactive dipyrro-methene-Cu(II) self-assembled monolayers: complexation reaction on the surface of gold electrodes Langmuir 24 11239 11245 10.1021/la801164f 10.1021/la801164f
20. I Szymańska C Orlewska D Janssen W Dehaen H Radecka 2008 Dipyrromethene-dodecanethiol self-assembled monolayers deposited onto gold electrodes Electrochim. Acta 53 7932 7940 10.1016/j.electacta.2008.06.002 10.1016/j.electacta.2008.06.002
21. K Kurza̧tkowska D Shpakovsky J Radecki H Radecka Z Jingwei E Milaeva 2009 Iron(III) porphyrin bearing 2,6-di-tert-butylphenol pendants deposited onto gold electrodes for amperometric determination of l-histidine Talanta 78 126 131 10.1016/j.talanta.2008.10.051 10.1016/j.talanta.2008.10.051
22. K Kurza̧tkowska E Dolusic W Dehaen K Sieroń-Stoltny A Sieroń H Radecka 2009 Gold electrode incorporating corrole as an ion-channel mimetic sensor for determination of dopamine Anal. Chem. 81 7397 7405 10.1021/ac901213h 10.1021/ac901213h
23. Jimenez, H.R.; Julve, M.; Faus, J.: A solution study of the protonation and deprotonation equilibria of 5,10,15,20-tetra(p-sulphonatophenyl) porphyrin. Stability of its magnesium(II), copper(II) and zinc(II) complexes. J. Chem. Soc.; Dalton Trans. 1945-1949 (1991). doi: 10.1039/DT9910001945
24. A Farjtabar F Gharib 2010 Solvent effect on protonation constants of 5,10,15,20-tetrakis(p-sulphonatophenyl) porphyrin in different aqueous solutions of methanol and ethanol J. Solut. Chem. 39 231 244 10.1007/s10953-010-9496-y 10.1007/s10953-010-9496-y 1:CAS:528:DC%2BC3cXivV2ktro%3D
25. A Mahammad JJ Weaver HB Gray M Abdelas Z Gross 2003 How acidic are corroles and why? Tetrahedron Lett. 44 2077 2079 10.1016/S0040-4039(03)00174-6 10.1016/S0040-4039(03)00174-6
26. J Shen J Shao Z Ou E Wenbo B Koszarna DT Gryko KM Kadish 2006 Electrochemistry and spectroelectrochemistry of meso-substituted free-base corroles in nonaqueous media: reactions of (Cor)H3, [(Cor)H4]+, and [(Cor)H2]- Inorg. Chem. 45 2251 2265 10.1021/ic051729h 10.1021/ic051729h 1:CAS:528:DC%2BD28XptV2rsg%3D%3D
27. Z Ou J Shen J Shao E Wenbo M Gałȩzowski DT Gryko KM Kadish 2007 Protonated free-base corroles: acidity, electrochemistry, and spectroelectrochemistry of [(Cor)H4]+, [(Cor)H5]2+, and [(Cor)H6]3+ Inorg. Chem. 46 2775 2786 10.1021/ic0617893 10.1021/ic0617893 1:CAS:528:DC%2BD2sXitFCmsb8%3D
28. T Kawaguchi H Yasuda K Shimazu 2000 Electrochemical quartz-crystal microbalance investigation of the reductive desorption of self-assembled monolayers of alkanethiols and mercaptoalkanoic acids on Au Langmuir 16 9830 9840 10.1021/la000756b 10.1021/la000756b 1:CAS:528:DC%2BD3cXotVejsr4%3D
29. T Kakiuchi M Iida S Imabayashi K Niki 2000 Double-layer capacitance titration of self-assembled monolayers of ω-functionalized alkanethiols on Au(111) surface Langmuir 16 5397 5401 10.1021/la991358f 10.1021/la991358f 1:CAS:528:DC%2BD3cXislygtb0%3D
30. a of SAM using an electrochemical titration method Electroanalysis 11 1108 1111 10.1002/(SICI)1521-4109(199911)11:15<1108::AID-ELAN1108>3.0. CO;2-Z 10.1002/(SICI)1521-4109(199911)11:15<1108::AID-ELAN1108>3.0.CO;2-Z 1:CAS:528:DyaK1MXnsVWlsL8%3D
31. a of 11-mercaptoundecanoic acid monolayers self-assembled on gold J. Phys. Chem. B 103 1676 1685 10.1021/jp983325z 10.1021/jp983325z 1:CAS:528:DyaK1MXhs1WnsLo%3D
32. a of carboxylic and amine-terminated alkane-thiols using surface plasmon resonance spectroscopy Langmuir 24 837 843 10.1021/la701760s 10.1021/la701760s 1:CAS:528:DC%2BD1cXis1OlsQ%3D%3D
33. H Ju Z Dai 2001 Effect of chain length on the surface proper-ties of ω-carboxy alkane thiol self-assembled monolayers Phys. Chem. Chem. Phys. 3 3769 3773 10.1039/b104570a
34. C Saby B Ortiz GY Champagne D Bèlanger 1997 Electrochemical modification of glassy carbon electrode using aromatic diazonium salts. 1. Blocking effect of 4-nitrophenyl and 4-carboxyphenyl groups Langmuir 13 6805 6813 10.1021/la961033o 10.1021/la961033o 1:CAS:528:DyaK2sXntlCltbY%3D
35. a values of benzoic acid-modified graphite and glassy carbon surfaces Langmuir 23 7847 7852 10.1021/la7005277 10.1021/la7005277 1:CAS:528:DC%2BD2sXmt1artbY%3D
36. R Schweiss D Pleul F Simon A Janke PB Welzel B Voit W Knoll C Werner 2004 Electrokinetic potentials of binary self-assembled monolayers on gold: acid-base reactions and double layer structure J. Phys. Chem. B 108 2910 2917 10.1021/jp035724m 10.1021/jp035724m 1:CAS:528:DC%2BD2cXptVKmtA%3D%3D
37. I Burgess B Seivewright BR Lennox 2006 Electric field driven protonation/deprotonation of self-assembled mono-layers of acid-terminated thiols Langmuir 22 4420 4428 10.1021/la052767g 10.1021/la052767g 1:CAS:528:DC%2BD28XjtVaqu7c%3D
38. TH Ngo W Van Rossom W Dehaen W Maes 2009 Reductive demetallation of Cu-corroles-a new protective strategy towards functional free-base corroles Org. Biomol. Chem. 7 439 443 10.1039/b819185a 10.1039/b819185a 1:CAS:528: DC%2BD1MXotVOrtw%3D%3D
39. TH Ngo F Puntoriero F Nastasi K Robeyns L Van Meervelt S Campagna W Dehaen W Maes 2010 Syn-thetic, structural and photophysical exploration of meso-pyrimidinyl-substituted AB2-corroles Chem. Eur. J. 16 5691 5705 10.1002/chem.201000008 1:CAS:528:DC%2BC3cXmt1ansLc%3D
40. Q Wang F Zhi W Wang X Xia X Liu F Meng Y Song C Yang X Lu 2009 Direct electron transfer of thiol-derivatized tetraphenylporphyrin assembled on gold electrodes in an aqueous solution J. Phys. Chem. C 113 9359 9367 10.1021/jp803725x 10.1021/jp803725x 1:CAS:528:DC%2BD1MXltFCqtbc%3D
41. J Shen Z Ou J Shao M Gałȩzowski DT Gryko KM Kadish 2007 Free-base corroles: determination of deprotonation constants in non-aqueous media J. Porphyr. Phtalocyanines 11 269 276 10.1142/S1088424607000321 1:CAS:528:DC%2BD2sXlvFKrt7Y%3D