Facile Synthesis and Photoluminescent Properties of Asymmetric Perylene Diimides Capable of Tuning Emission Colors in Polymeric Matrices

Kyosuke Isoda; Natsuki Yamaguchi; Shogo Morisako

doi:10.1002/asia.202400422

Facile Synthesis and Photoluminescent Properties of Asymmetric Perylene Diimides Capable of Tuning Emission Colors in Polymeric Matrices

Chem Asian J. 2024 May 16:e202400422. doi: 10.1002/asia.202400422. Online ahead of print.

Authors

Kyosuke Isoda¹, Natsuki Yamaguchi², Shogo Morisako³

Affiliations

¹ Sagami Chemical Research Center: Koeki Zaidan Hojin Sagami Chuo Kagaku Kenkyujo, Organic Materials Chemistry Group, 2743-1 Hayakawa, Ayase, 252-1193, Kanagawa, JAPAN.
² Kitasato University - Sagamihara Campus, Department of Chemistry, JAPAN.
³ Sagami Chemical Research Center, Organic materials group, JAPAN.

PMID: 38757349
DOI: 10.1002/asia.202400422

Abstract

We report the facile synthesis of asymmetric perylene diimides (asym-PDIs) using readily available reagents, demonstrating their distinct photoluminescent properties. In CHCl3, asym-PDIs exhibit higher solubility compared to traditional perylene dyes, of which solubilities can be varied by substituent selections. Among them, UV-vis absorption spectra of CPE in CHCl3 solution displayed no aggregate peaks in the ground state, maintaining high photoluminescent quantum yields. Also, CPE can be readily dispersed into poly(methyl methacrylate) PMMA (CPE-PMMA), forming thin films without aggregate formation. Importantly, the emission color of CPE-PMMA thin films significantly changes with the addition of polycyclic aromatic hydrocarbons (PAHs). These color changes should be strongly correlated with the HOMO level of the added PAHs.

Keywords: Emission color tuning; Photophysical properties; Polycyclic hydrocarbons; Polymer-dispersed thin film; asymmetric Perylene Diimides.