Synthesis of Silatrane-Containing Organic Sensitizers as Precursors for the Silyloxyl Anchoring Group in Dye-Sensitized Solar Cells

Year: 2017

Authors: Bessi M., Monini M., Calamante M., Mordini A., Sinicropi A., Basosi R., Di Donato M., Foggi P., Iagatti A., Zani L., Reginato G.

Autors Affiliation: Istituto di Chimica dei Composti Organometallici (CNR-ICCOM), Via Madonna del Piano 10, 50019 Sesto Fiorentino, Italy; Dipartimento di Biotecnologie, Chimica e Farmacia, Università degli Studi di Siena, Via A. Moro 2, 53100 Siena, Italy; Dipartimento di Chimica ‘U. Schiff’, Università degli Studi di Firenze, Via della Lastruccia 13, 50019 Sesto Fiorentino, Italy; Istituto Nazionale di Ottica (CNR-INO), Largo Enrico Fermi 6, 50125 Florence, Italy; Dipartmento di Chimica, Università degli studi di Perugia, via Elce di Sotto 8, 06123 Perugia, Italy; LENS (European Laboratory for Non-Linear Spectroscopy), Via N. Carrara 1, 50019 Sesto Fiorentino, Italy

Abstract: A series of organic D-?-A dyes, endowed with different silicon-based anchoring groups, has been prepared to assess the stability of such anchoring moieties on nanocrystalline TiO2 in dye-sensitized solar cells. Due to the difficulties encountered in finding a reliable and robust preparation protocol to obtain pure trialkoxysilanes, replacement with a silatrane moiety was evaluated. It was found that the silatrane group could be easily introduced on three different molecular scaffolds by using a simple amide coupling reaction mediated by EDC-Cl. Furthermore, the spectroscopic properties and anchoring mode on nanocrystalline TiO2 of the silatrane dyes were found to be nearly identical to those of the trialkoxysilane compounds, and both gave a much more stable attachment to the semiconductor compared with their cyano­acrylic acid counterpart, as shown by desorption experiments.


Volume: 49 (17)      Pages from: 3975  to: 3984

KeyWords: Nanocrystalline silicon; Nanocrystals; Solar cells; Titanium dioxide; Ultraviolet visible spectroscopy, Anchoring groups; Molecular scaffolds; Nano-crystalline TiO; Organic dye; siltarane; Spectroscopic property; trialkoxysilane; UV/ Vis spectroscopy, Dye-sensitized solar cells, 2 cyano 3 [8 [4 (diphenylamino)styryl] 3,3 dipentyl 3,4 dihydro 2h thieno[3,4 b][1,4]dioxepin 6 yl] n [4 (trimethoxysilyl)phenyl]acrylamide; 3 [5 [ 4 [bis[4 (hexyloxy)phenyl]amino]styryl]thiophen 2 yl] 2 cyano n (4 iodophenyl)acrylamide; 3 [5 [ 4 [bis[4 (hexyloxy)phenyl]amino]styryl]thiophen 2 yl] 2 cyano n [(4 triethoxysilyl)phenyl]acrylamide; 3 [[5 4 [bis[4 (hexyloxy)phenyl]amino]styryl]thiophen 2 yl] 2 cyano n [3 (triethoxysilyl)propyl]acrylamide; amide; cyanoacrylate derivative; dye; molecular scaffold; n [4 (2,8,9 trioxa 5 aza 1 silabicyclo[3.3.3]undecan 1 yl)phenyl] 2 cyano 3 [8 [4 (diphenylamino)styryl] 3,3 dipentyl 3,4 dihydro 2h thieno[3,4 b][1,4]dioxepin 6 yl]acrylamide; n [4 (2,8,9 trioxa 5 aza 1 silabicyclo[3.3.3]undecan 1 yl)phephenyl] 3 [5 [4 [bis[4 (hexyloxy)phenyl]amino]styryl]thiophen 2 yl] 2 cyanoacrylamide; nanocrystal; organosilicon derivative; silatrane derivative; siloxane; titanium dioxide; trialkoxysilane derivative; unclassified drug, Article; chemical binding; chemical reaction; chemical structure; covalent bond; desorption; electrochemical analysis; precursor; proton transport; purification; semiconductor; sensitization; solar cell; synthesis; ultraviolet spectroscopy
DOI: 10.1055/s-0036-1588836

Citations: 2
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