Push-Pull N, N-Diphenylhydrazones Bearing Bithiophene or Thienothiophene Spacers as Nonlinear Optical Second Harmonic Generators and as Photosensitizers for Nanocrystalline TiO2 Dye-Sensitized Solar Cells

• Tipo: Artigo em Revista Científica Internacional
• Data: 2018-10-09

Autores

Dzmitry Ivanou (Autor) FEUP; Adélio Mendes (Autor) FEUP; Sara S. M. Fernandes (Autor) Outra; Michael Belsley (Autor) Outra; Ana I. Pereira (Autor) Outra; Licínia L. G. Justino (Autor) Outra; Hugh D. Burrows (Autor) Outra; M. Manuela M. Raposo (Autor) Outra

Revista

Título: ACS Omega

Vol. 3 Nº 10

Páginas: 12893-12904

Editora: American Chemical Society

Indexação

ISI Web of Knowledge - 1 Citação

ISI Web of Science

Scopus - 10 Citações

Projetos Associados

SunStorage - Recolha e armazenamento de energia solar

Outras Informações

ID Authenticus: P-00P-REM

DOI: 10.1021/acsomega.8b01045

Abstract (EN): A series of push-pull heterocyclic N,N-diphenylhydrazones were prepared to study the effect of structural modifications (different pi-spacers and electron-withdrawing groups) on the optical (linear and nonlinear) and lectronic properties of the molecules. The photovoltaic response of dye-sensitized solar cells assembled using nanocrystalline titania photosensitized with the synthesized dyes was also studied. These heterocyclic push-pull conjugated dyes involve N,N-diphenylhydrazones as electron donors linked to bithiophene or thieno[3,2-b]thiophene spacers and were functionalized with carboxylic acid, cyanoacetic acid, or dicyanovinyl acceptor groups. A combination of Suzuki-Miyaura cross-coupling, Vilsmeier formylation, and condensation reactions was used to synthesize the intermediates and final products. Density functional theory (DFT) and time dependent-DFT calculations were used to obtain information on conformation, electronic structure, and electron distribution, both for the free dyes and those adsorbed on TiO2. The results of this multidisciplinary study indicate that dyes 5b and 6b have the strongest second-order nonlinear optical response with hyperpolarizability values in the range of beta = 2330 X 10(-3) to 2750 X 10(-3) esu, whereas photovoltaic power conversion efficiencies reach values in the range of 0.7-3.0% for dyes 5a-b and 7c and were enhanced by coadsorbing deoxycholic acid (0.8-5.1%).

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 12