Amino-based Anthocyanin Dyes: Exploring the Relation Between Structural Rigidification and Back-Electron Transfer

Ana Lucia Pinto^a, Patríca Máximo^a, João Pina^b, Giuseppe Calogero^c, César A. T. Laia^a, A. Jorge Parola^a, J. Carlos Lima^a

^aLAQV-REQUIMTE, Chemistry Department, NOVA School of Science and Technology, Campus de Caparica, 2829-516, Caparica, Portugal.

^bUniversity of Coimbra, Coimbra Chemistry Centre, Department of Chemistry, Rua Larga, 3004-535 Coimbra, Portugal.

^cCNR, Instituto per i Processi Chimico-Fisici, Sede di Messina, Salita Sperone, C. da Papardo, I-98158 Faro Superiore Messina, Italy.

International Conference on Hybrid and Organic Photovoltaics
Proceedings of International Conference on Hybrid and Organic Photovoltaics (HOPV22)

València, Spain, 2022 May 19th - 25th

Organizers: Pablo Docampo, Eva Unger and Elizabeth Gibson

Contributed talk, Ana Lucia Pinto, presentation 135
DOI: https://doi.org/10.29363/nanoge.hopv.2022.135
Publication date: 20th April 2022

The use of natural/bio-inspired pigments as sensitizers in Dye-Sensitized Solar Cells (DSSCs) has come to be a worthwhile substitute to the inorganic/organic sensitizers due to the cost-effectiveness enhancement and reduced environmental pollution risks.[1]The first reported DSSC using a natural anthocyanin (cyanidin-3-O-glucoside) displayed a conversion yield of 0.56 % and paved the way for sustainable DSSCs based on renewable resources.[2]The structural modification of this natural compound, through the insertion of a stronger electron-donating moiety (7-diethylamino-3’,4’-dihydroxyflavylium), led to an improved efficiency of 2.15 %, proving the potential of bio-inspired compounds for energy applications.[3] Herein, a series of new amino-based flavylium derivatives inspired in compound 7-diethylamino-3’,4’-dihydroxyflavylium were designed and synthesized, focusing on studying the impact of rigidifying the flavylium structure, as well as the structure of the electron-donating moiety, by replacing diethylamine by a julolidine moiety. Despite being a stronger electron-donor, the current intensity vs. potential properties of photoanodes containing these dyes presented lower photocurrent for julolidine-based compounds, possibly attributable to the presence of increased back-electron transfer (BET). These results pointed to evidence that has been overlooked in the study of anthocyanin derivatives in energy applications, that is the impact of the structure in the back-electron transfer processes that might hinder the photocurrent. This is the first study that puts in evidence how BET processes can affect the performance of this family of compounds.

References:

[1] Bartolotta, A.; Calogero, G. Dye-sensitized solar cells: from synthetic dyes to natural pigments in Solar Cells and Light Management 2020, 107, Enrichi, F.; Righini, G. C. Amsterdam, Elsevier Ltd.

[2] Cherepy, N. J.; Smestad, G. P.; Grätzel, M.; Zhang, J. Z. Ultrafast Electron Injection: Implications for a Photoelectrochemical Cell Utilizing an Anthocyanin Dye-Sensitized TiO2 Nanocrystalline Electrode. J. Phys. Chem. B. 1997, 101, 9342–9351.

[3] Calogero, G.; Sinopoli, A.; Citro, I.; Di Marco, G.; Petrov, V.; Diniz, A. M.; Parola, A. J.; Pina, F. Synthetic analogues of anthocyanins as sensitizers for dye-sensitized solar cells. Photochem. Photobiol. Sci. 2013, 12, 883–94.

Acknowledgements:

FCT/MCTES is acknowledged for financial support through the project PD/00184/2012/PDQS, the grant PD/BD/135087/2017 (ALP) and the Associate Laboratory for Green Chemistry- LAQV (UIDB/50006/2020 and UIDP/50006/2020).

nanoGe is a prestigious brand of successful science conferences that are developed along the year in different areas of the world since 2009. Our worldwide conferences cover cutting-edge materials topics like perovskite solar cells, photovoltaics, optoelectronics, solar fuel conversion, surface science, catalysis and two-dimensional materials, among many others.

MATSUS

Previously nanoGe Spring Meeting (NSM) and nanoGe Fall Meeting (NFM), MATSUS is a multiple symposia conference focused on a broad set of topics of advanced materials preparation, their fundamental properties, and their applications, in fields such as renewable energy, photovoltaics, lighting, semiconductor quantum dots, 2-D materials synthesis, charge carriers dynamics, microscopy and spectroscopy semiconductors fundamentals, etc.

International Conference on Hybrid and Organic Photovoltaics

International Conference on Hybrid and Organic Photovoltaics (HOPV) is celebrated yearly in May. The main topics are the development, function and modeling of materials and devices for hybrid and organic solar cells. The field is now dominated by perovskite solar cells but also other hybrid technologies, as organic solar cells, quantum dot solar cells, and dye-sensitized solar cells and their integration into devices for photoelectrochemical solar fuel production.

Asia-Pacific International Conference on Perovskite, Organic Photovoltaics and Optoelectronics

The main topics of the Asia-Pacific International Conference on Perovskite, Organic Photovoltaics and Optoelectronics (IPEROP) are discussed every year in Asia-Pacific for gathering the recent advances in the fields of material preparation, modeling and fabrication of perovskite and hybrid and organic materials. Photovoltaic devices are analyzed from fundamental physics and materials properties to a broad set of applications. The conference also covers the developments of perovskite optoelectronics, including light-emitting diodes, lasers, optical devices, nanophotonics, nonlinear optical properties, colloidal nanostructures, photophysics and light-matter coupling.

International Conference on Perovskite Thin Film Photovoltaics Perovskite Photonics and Optoelectronics

The International Conference on Perovskite Thin Film Photovoltaics Perovskite Photonics and Optoelectronics (NIPHO) is the best place to hear the latest developments in perovskite solar cells as well as on recent advances in the fields of perovskite light-emitting diodes, lasers, optical devices, nanophotonics, nonlinear optical properties, colloidal nanostructures, photophysics and light-matter coupling.