Effect of Different Substitutions at the 1,7-Bay Positions of Perylenediimide Dyes on Their Optical and Laser Properties

• Published in: Molecules (Basel, Switzerland) Vol. 28; no. 19; p. 6776
• Main Authors: Zink-Lorre, Nathalie, Ramírez, Manuel G, Pla, Sara, Boj, Pedro G, Quintana, José A, Villalvilla, José M, Sastre-Santos, Ángela, Fernández-Lázaro, Fernando, Díaz-García, María A
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 23.09.2023; MDPI
• Subjects: amplified spontaneous emission; Benzene; Lasers; Light emitting diodes; Optical properties; organic lasers; perylenediimides; Photoluminescence; Polymers; Spectrum analysis; Massachusetts; Spain; amplified spontaneous emission; photoluminescence; organic lasers; perylenediimides
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules28196776

Perylenediimide (PDI) compounds are widely used as the active units of thin-film organic lasers. Lately, PDIs bearing two sterically hindering diphenylphenoxy groups at the 1,7-bay positions have received attention because they provide a way to red-shift the emission with respect to bay-unsubstituted PDIs, while maintaining a good amplified spontaneous emission (ASE) performance at high doping rates. Here, we report the synthesis of a series of six PDI derivatives with different aryloxy groups ( to ) or ethoxy groups ( ) at the 1,7 positions of the PDI core, together with a complete characterization of their optical properties, including absorption, photoluminescence, and ASE. We aim to stablish structure-property relationships that help designing compounds with optimized ASE performance. Film experiments were accomplished at low PDI concentrations in the film, to resemble the isolated molecule behaviour, and at a range of increasing doping rates, to investigate concentration quenching effects. Compounds and , bearing substituents in the 2' positions of the benzene ring (the one contiguous to the linking oxygen atom) attached to the 1,7 positions of the PDI core, have shown a better threshold performance, which is attributed to conformational (steric) effects. Films containing show dual ASE.