Phthalocyanines and naphthalocyanines: synthesis and characterization of amphiphil...
| Full text | |
| Author(s): |
de Souza, Thalita F. M.
[1]
;
Antonio, Felipe C. T.
[1]
;
Zanotto, Mateus
[1]
;
Homem-de-Mello, Paula
[1]
;
Ribeiro, Anderson O.
[1]
Total Authors: 5
|
| Affiliation: | [1] Univ Fed ABC UFABC, Ctr Ciencias Nat & Humanas, Ave Estados 5001, Bloco B, BR-09210170 Santo Andre, SP - Brazil
Total Affiliations: 1
|
| Document type: | Journal article |
| Source: | Journal of the Brazilian Chemical Society; v. 29, n. 6, p. 1199-1209, JUN 2018. |
| Web of Science Citations: | 2 |
| Abstract | |
The photophysical and photochemical properties of phthalocyanine and naphthalocyanine with similar structures were studied in solution and with density-functional theory (DFT) computational method. The extended pi-conjugated system in naphthalocyanines causes a bathochromic shift in UV-Vis, emission and excitation bands, and promotes lesser generation of singlet oxygen in solution when compared to phthalocyanines. Time dependent DFT (TD-DFT) calculations point out the molecular orbitals involved in Q-band transition, corresponding to highest occupied molecular orbital (HOMO) to lowest unoccupied molecular orbital (LUMO) transition with a concentration of charge along x-axis, while the transition to LUMO+1 is in y-axis direction. The presence of tert-butyl substituents does not affect the molecular orbitals shape. but affect their energies. Aggregation studies in dimethyl sulfoxide (DMSO):water solutions showed that naphthalocyanines studied have more aggregation tendency than the phthalocyanines. DFT studies indicated that stacked-dimers are preferred to rotated-stacked conformation due the interaction between Zn-II and nitrogen atom from different monomers. (AU) | |
| FAPESP's process: | 14/18527-8 - Phthalocyanines and naphthalocyanines: synthesis and characterization of amphiphilic macrocyles for photodynamic therapy |
| Grantee: | Anderson Orzari Ribeiro |
| Support type: | Regular Research Grants |
| FAPESP's process: | 12/50680-5 - Photosensitization in life sciences |
| Grantee: | Mauricio da Silva Baptista |
| Support type: | Research Projects - Thematic Grants |