Synthesis 2017; 49(17): 3975-3984
DOI: 10.1055/s-0036-1588836
paper
© Georg Thieme Verlag Stuttgart · New York

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

Matteo Bessi
a  Istituto di Chimica dei Composti Organometallici (CNR-ICCOM), Via Madonna del Piano 10, 50019 Sesto Fiorentino, Italy   eMail: [email protected]
b  Dipartimento di Biotecnologie, Chimica e Farmacia, Università degli Studi di Siena, Via A. Moro 2, 53100 Siena, Italy
,
Marco Monini
a  Istituto di Chimica dei Composti Organometallici (CNR-ICCOM), Via Madonna del Piano 10, 50019 Sesto Fiorentino, Italy   eMail: [email protected]
,
Massimo Calamante
a  Istituto di Chimica dei Composti Organometallici (CNR-ICCOM), Via Madonna del Piano 10, 50019 Sesto Fiorentino, Italy   eMail: [email protected]
c  Dipartimento di Chimica ‘U. Schiff’, Università degli Studi di Firenze, Via della Lastruccia 13, 50019 Sesto Fiorentino, Italy
,
Alessandro Mordini
a  Istituto di Chimica dei Composti Organometallici (CNR-ICCOM), Via Madonna del Piano 10, 50019 Sesto Fiorentino, Italy   eMail: [email protected]
c  Dipartimento di Chimica ‘U. Schiff’, Università degli Studi di Firenze, Via della Lastruccia 13, 50019 Sesto Fiorentino, Italy
,
Adalgisa Sinicropi
a  Istituto di Chimica dei Composti Organometallici (CNR-ICCOM), Via Madonna del Piano 10, 50019 Sesto Fiorentino, Italy   eMail: [email protected]
b  Dipartimento di Biotecnologie, Chimica e Farmacia, Università degli Studi di Siena, Via A. Moro 2, 53100 Siena, Italy
,
Riccardo Basosi
a  Istituto di Chimica dei Composti Organometallici (CNR-ICCOM), Via Madonna del Piano 10, 50019 Sesto Fiorentino, Italy   eMail: [email protected]
b  Dipartimento di Biotecnologie, Chimica e Farmacia, Università degli Studi di Siena, Via A. Moro 2, 53100 Siena, Italy
,
Mariangela Di Donato
c  Dipartimento di Chimica ‘U. Schiff’, Università degli Studi di Firenze, Via della Lastruccia 13, 50019 Sesto Fiorentino, Italy
d  INO, Istituto Nazionale di Ottica, Largo Enrico Fermi 6, 50125 Florence, Italy
f  LENS (European Laboratory for Non-Linear Spectroscopy), Via N. Carrara 1, 50019 Sesto Fiorentino, Italy
,
Paolo Foggi
a  Istituto di Chimica dei Composti Organometallici (CNR-ICCOM), Via Madonna del Piano 10, 50019 Sesto Fiorentino, Italy   eMail: [email protected]
d  INO, Istituto Nazionale di Ottica, Largo Enrico Fermi 6, 50125 Florence, Italy
e  Dipartmento di Chimica, Università degli studi di Perugia, via Elce di Sotto 8, 06123 Perugia, Italy
f  LENS (European Laboratory for Non-Linear Spectroscopy), Via N. Carrara 1, 50019 Sesto Fiorentino, Italy
,
Alessandro Iagatti
d  INO, Istituto Nazionale di Ottica, Largo Enrico Fermi 6, 50125 Florence, Italy
f  LENS (European Laboratory for Non-Linear Spectroscopy), Via N. Carrara 1, 50019 Sesto Fiorentino, Italy
,
Lorenzo Zani
a  Istituto di Chimica dei Composti Organometallici (CNR-ICCOM), Via Madonna del Piano 10, 50019 Sesto Fiorentino, Italy   eMail: [email protected]
,
Gianna Reginato*
a  Istituto di Chimica dei Composti Organometallici (CNR-ICCOM), Via Madonna del Piano 10, 50019 Sesto Fiorentino, Italy   eMail: [email protected]
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Publikationsverlauf

Received: 14. März 2017

Accepted after revision: 28. April 2017

Publikationsdatum:
07. Juni 2017 (online)


Abstract

A series of organic D-π-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.

Supporting Information

 
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