Highly Efficient Photoninitiators Based on 4H‐Pyranylidene Derivatives for Two‐Photon Laser Printing

Author:

Royo Raquel1,Mainik Philipp2,Benitez‐Martin Carlos3,Andreu Raquel1,Blasco Eva2ORCID,Najera Francisco45,Villacampa Belén6

Affiliation:

1. Instituto de Nanociencia y Materiales de Aragón (INMA)‐Departamento de Química Orgánica CSIC‐Universidad de Zaragoza Zaragoza 50009 Spain

2. Institute for Molecular Systems Engineering and Advanced Materials (IMSEAM) Heidelberg University im Neuenheimer Feld 225 69120 Heidelberg Germany

3. Department of Chemistry and Chemical Engineering Chalmers University of Technology Gothenburg 41296 Sweden

4. Departamento de Química Orgánica Universidad de Málaga Campus Teatinos s/n Málaga 29071 Spain

5. Instituto de Investigación Biomédica de Málaga y Plataforma en Nanomedicina–IBIMA Plataforma Bionand, Parque Tecnológico de Andalucía Málaga 29590 Spain

6. Instituto de Nanociencia y Materiales de Aragón (INMA)‐Departamento de Física de la Materia Condensada CSIC‐Universidad de Zaragoza Zaragoza 50009 Spain

Abstract

AbstractA series of four donor–acceptor–donor derivatives bearing 4H‐pyranylidene and 4‐methylcyclohexan‐1‐one units as donor and acceptor groups respectively is designed, synthesized, and photophysically characterized. Both experimental and theoretical studies reveal good two‐photon absorption (2PA) properties for these systems. Decoration of the exocyclic position of the 4H‐pyranylidene moiety with a thiophene ring results in high 2PA cross‐section values (σ2PA) ≈700 nm, and remarkably, in the region between 900 and 1000 nm. Furthermore, all chromophores are evaluated as photoinitiators (PIs) for two‐photon‐laser printing at 780 nm, showing superior performance compared to the commonly used commercially available PI, phenylbis(2,4,6‐trimethylbenzoyl)phosphine oxide. Among the studied PIs, the ones equipped with a thiophene unit at the exocyclic position of the 4H‐pyranylidene moiety exhibit the highest efficiency, enabling fast printing using low laser powers with even lower concentrations of PI. Overall, this study shows the great potential of this new class of PIs for application in the field of 3D nanoprinting.

Funder

Ministerio de Ciencia e Innovación

Universidad de Zaragoza

Publisher

Wiley

Subject

Industrial and Manufacturing Engineering,Mechanics of Materials,General Materials Science

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