Molecular Synthesis Group

Responsible	Fernando Fernández Lázaro
Website	http://quimicaorganica.umh.es

RESEARCH SUMMARY

Since their discovery, perylenediimides (PDIs) have attracted much attention thanks to their strong absorption of visible light, their high fluorescence quantum yields and their thermal, chemical and photochemical stabilities. Another turn of the screw occurred with the advent of the organic optoelectronics, as PDIs revealed themselves as excellent electron transporting materials with high electron affinities. As a result of all the above, they have been exhaustively studied in solar cells (organic, dye-sensitized and perovskite-based), light-emitting devices, lasers, field-effect transistors, artificial photosynthetic systems, sensors and in different biological applications.

Scheme of a PDI-based LED prepared in our group.

RESEARCH LINES

Line1: New methods for synthesis and modification of perylenediimides

The wide variety of applications of PDIs requires the fine-tuning of the molecular packing and the optical and electronic properties, which may be accomplished by introduction of suitable substituents in their structure. In our group we are interested in the search for new and more efficient ways to modify the chemical structure of PDIs, thus allowing the tailoring of the properties for the desired application.

síntesis molecular línea 1

The introduction of the adequate substituents on the PDI scaffold allows for the modification of the properties of PDIs as, for example, the absorption spectrum and, hence, the colour in solution.

Line 2: Organic laser dyes

PDIs represent an outstanding choice for organic lasers because they exhibit not only good emission properties and wavelength tunability, but also good thermal and optical stabilities and high electron mobility. In addition, optical and electronic properties of PDIs can be tailored by introducing the adequate substituents, resulting in high-performance solid state lasers.

síntesis molecular línea 2

Scheme of a laser prepared with one of our PDIs.

Line 3: Synthesis of organic materials for photovoltaics

Our group is actively working in the incorporation of perylenediimides as photoactive components in different solar cell devices: p–n organic solar cells, as non-fullerene acceptors in bulk heterojunction solar cells, as photosensitisers in dye-sensitised solar cells, in perovskite solar cells, and also as interlayers acting as either electron- or hole-transporting materials. As a previous step, we investigate the photophysical properties of PDIs regarding to photoinduced energy and/or electron transfer. We are also interested in the use of PDIs in artificial photosynthetic systems.

síntesis molecular línea 3

Name	Position	e-mail	ORCID
Fernando Fernández Lázaro	Full Professor		0000-0002-4598-6024
Enrique Font Sanchis	Associate Professor		0000-0002-5082-3107
Ana María Gutiérrez Vílchez	PhD. Assistant Lecturer		0000-0002-9310-4022
Nathalie Zink Lorre	PhD. Assistant Lecturer		0000-0003-3081-995X
Jose Garcés Garcés	PhD Student		0000-0002-7637-3140

A. Scalabre, A. M. Gutiérrez-Vílchez, Á. Sastre-Santos, F. Fernández-Lázaro, D. M. Bassani y R. Oda
Supramolecular Induction of Topological Chirality fron Nanoscale Helical Silica Scaffolds to Achiral Molecular Chromophores
J. Phys. Chem. C 124, 23839-23843 (2020)

I. Papadopoulos, D. Gutiérrez-Moreno, P. M. McCosker, R. Casillas, P. A. Keller, Á. Sastre-Santos, T. Clark, F. Fernández-Lázaro y D. M. Guldi
Perylene-Monoimides: Singlet Fission Down-Conversion Competes with Up-Conversion by Geminate Triplet-Triplet Recombination
J. Phys. Chem. A 124, 5727–5736 (2020)

E. J. Canto-Aguilar, D. Gutiérrez-Moreno, Á. Sastre-Santos, D. Morikawa, M. Abe, F. Fernández-Lázaro, G. Oskam y S. Mori.
Identification of the Loss Mechanisms in TiO2 and ZnO Solar Cells Based on Blue, Piperidinyl-Substituted, Mono-Anhydride Perylene Dyes
Electrochim. 355, 136638 1-11 (2020)

N. Zink-Lorre, E. Font-Sanchis, Á. Sastre-Santos y F. Fernández-Lázaro
Perylenediimides as More than Just Non-Fullerene Acceptors: Versatile Components in Organic, Hybrid and Perovskite Solar Cells
Chem. Commun. 56, 3824-3838 (2020)

V. Navarro-Pérez, A. M. Gutiérrez-Vílchez, J. Ortiz, Á. Sastre-Santos, F. Fernández-Lázaro, S. Seetharaman, M. J. Duffy, P. A. Karr y F. D’Souza
A Zinc Phthalocyanine-Benzoperylenetriimide Conjugate for Solvent Dependent Ultrafast Energy vs. Electron Transfer
Chem. Commun. 55, 14946-14949 (2019)

N. Zink-Lorre, A. Doncel-Giménez, E. Font-Sanchis, J. Calbo, A. Sastre-Santos, E. Ortí y F. Fernández-Lázaro
Diels-Alder Reaction on Perylenediimides: Synthesis and Theoretical Study of Core-Expanded Diimides
Org. Chem. Front. 6, 2860-2871 (2019)

D. Gutiérrez-Moreno, A. Sastre-Santos y F. Fernández-Lázaro
Direct Amination and N-Heteroarylation of Perylenediimides
Org. Chem. Front. 6, 2488-2499 (2019)

N. Zink-Lorre, E. Font-Sanchis, S. Seetharaman, P. A. Karr, A. Sastre-Santos, F. D’Souza y F. Fernández-Lázaro
Directly Linked Zinc Phthalocyanine-Perylenediimide Dyads and a Triad for Ultrafast Charge Separation
Chem.-Eur. J. 25, 10123-10132 (2019)

R. Muñoz-Mármol, N. Zink-Lorre, J. M. Villalvilla, P. G. Boj, J. A. Quintana, C. Vázquez, A. Anderson, M. J. Gordon, Á. Sastre-Santos, F. Fernández-Lázaro y M. A. Díaz-García
Influence of Blending Ratio and Polymer Matrix on the Lasing Properties of Perylenediimide Dyes
J. Phys. Chem. C 122, 24896-24906 (2018)

D. Gutiérrez-Moreno, Á. Sastre-Santos y F. Fernández-Lázaro
Synthesis of Bay-Triaminosubstituted Perylenediimides
Org. Chem. Front. 5, 1830-1834 (2018)

Perylene diamides: photoinduced electron transfer in multichromophoric systems, singlet fission and lasers. Preparation of PDI-based SURMOFs. (PID2019-109200GB-I00). Funding agency: State Research Agency / Ministry of Science and Innovation. Duration: 01/06/2020-31/05/2023.