Hierarchical dependence of porphyrin self-aggregation: Controlling and exploiting the complexity

Journal of Porphyrins and Phthalocyanines

Volumn 14, Issue 8, 2010, Pages 708-712

  Escudero, Carlos ^a   D'Urso, Alessandro ^b   Lauceri, Rosaria ^c   Bonaccorso, Carmela ^b   Sciotto, Domenico ^b   Di Bella, Santo ^b   El Hachemi, Zoubir ^a   Crusats, Joaquim ^a   Ribó, Josep M ^a   Purrello, Roberto ^b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITY OF CATANIA   (Italy)

^c CNR   (Italy)

Author keywords

calix 4 arene; hierarchy; J aggregate; RLS

Indexed keywords

EID: 78149433622     PISSN: 10884246     EISSN: None     Source Type: Journal    
DOI: 10.1142/S1088424610002525     Document Type: Conference Paper

References (26)

1. Ono K, Yoshizawa M, Kato T, Watanabe K and Fujita M. Angew. Chem. Int. Ed. 2007; 46: 1803-1806.
2. Sugimoto T, Sada K, Tateishi Y, Suzuki T, Sei Y, Yamaguchi K and Shinkai S. Tetrahedron Lett. 2005; 46: 5347-5350.
3. Fiammengo R, Timmerman P, Huskens J, Versluis K, Heck AJR and Reinhoudt DN. Tetrahedron 2002; 58: 757-764.
4. a) Gulino FG, Lauceri R, Frish L, Evan-Salem T, Cohen Y, De Zorzi R, Geremia S, Di Costanzo L, Randaccio L, Sciotto D and Purrello R. Chem. Eur. J. 2006; 12: 2722 2729.
5. b) Moschetto G, Lauceri R, Gulino FG, Sciotto D and Purrello R. J. Am. Chem. Soc. 2002; 124: 14536-14537.
6. c) Di Costanzo L, Geremia S, Randaccio L, Purrello R, Lauceri R, Sciotto D, Gulino FG and Pavone V. Angew. Chem. Int. Ed. 2001; 40: 4245-4247.
7. (a) Castriciano MA, Romeo A, Villari V, Micali N and Monsù Scolaro L. J. Phys. Chem. 2003; 107: 8765-8771.
8. (b) Koti ASR, Taneja J, Periasamy N. Chem. Phys. Lett. 2003; 375: 171-176.
9. De Napoli M, Nardis S, Paolesse R, Vicente MGH, Lauceri R and Purrello R. J. Am. Chem. Soc. 2004; 126: 5934-5935.
10. a) Pasternack RF, Huber PR, Boyd P, Engasser G, Francesconi L, Gibbs E, Fasella P, Cerio VG and Hinds LdeC. J. Am. Chem. Soc. 1972; 94: 4511-4517.
11. b) Akins DL, Zhu HR and Guo C. J. Phys. Chem. 1996; 100: 5420-5425.
12. Ribó JM, Crusats J, Farrera JA and Valero ML. J. Chem. Soc. Chem. Commun. 1994; 9: 681-682.
13. a) Escudero C, El-Hachemi Z, Crusats J and Ribó JM. J. Porphyrins Phthalocyanines 2006; 9: 852-863.
14. b) Escudero C, Crusats J, Díez-Pérez I, El-Hachemi Z and Ribó JM. Angew. Chem. Int. Ed. 2006; 45: 8032-8035.
15. For pH values close to 2.0, aggregation is also observed in solution in the absence of salt. This is mostly likely because of the ionic strength due to the addition of acid.
16. The behavior of the system is much more complicated when dealing with concentrations in solution higher than 3 μM. Self-aggregation depends on different factors: concentration of 1 both in the stock and in the working solutions, aging of the stock solution, addition order of reagents and pH. This makes the study of the system very complicated owing to a possible cross-dependence of the above parameters. These studies are in progress.
17. The very first evidences of J-aggregation was observed only after 24 hours.
18. Pasternack RF and Collings PJ. Science 1995; 269: 935-939.
19. Spectrum (B) is obtained when 1 is added to a 3 ml of NaCl acidified solution and (A) when NaCl is added as last component. In both procedures, fast mixing was always assured by strong manual shaking.
20. We hypothesize that the aggregates of unprotonated 1 have a face-to-face H-like structure which allow for minimizing the charge repulsion. This hypothesis accounts for the very rapid dissociation after protonation in the absence of salt (owing to repulsion between the positive inner cores) and for the slow formation of J-aggregates that can form only after a H- to J-rearrangement.
21. It has been previously shown that cationic porphyrins form quite strong 1:4 (porphyrin:calixarene) complexes with anionic calixarenes where porphyrin meso-groups point toward the calixarene cavity [4].
22. The approach presented above is the only one that allows for the use of 3 as sensor. In fact, in another experiment we have formed the 1:4 species at pH 3 in the absence of NaCl to avoid J-aggregation. However, addition of chromate is accompanied by J-aggregate formation that falsified chromate determination. The sensitivity of these complexes toward other anions is currently under investigation.
23. Parker D. (Ed.) Macrocycle Synthesis, Oxford University Press: New York, 1996.
24. Jakobi RA, Böhmer V, Grüttner C, Kraft D and Vogt W. New J. Chem. 1996; 20: 493-501.
25. Yang X, McBranch D, Swanson B and Li D. Angew. Chem. Int. Ed. Eng. 1996; 35: 538-540.
26. Sgarlata C, Bonaccorso C, Gulino FG, Zito V, Arena G and Sciotto D, Tetrahedron Lett. 2009; 50: 1610-1613.