Simple Perylene Diimide Cyclohexane Derivative With Combined CPL and TPA Properties

Overview

Journal Front Chem

Specialty Chemistry

Date 2020 May 7

PMID 32373591

Citations 4

Authors

Pablo Reine

Ana M Ortuno

Ines F A Mariz

Maria Ribagorda

Juan M Cuerva

Araceli G Campana

Emerlinda Macoas

Delia Miguel

Affiliations

Soon will be listed here.

Abstract

In this work we describe the linear and non-linear (chiro)optical properties of an enantiopure bis-perylenediimide (PDI) cyclohexane derivative. This compound exhibits upconversion based on a two-photon absorption (TPA) process with a cross-section value of 70 GM together with emission of circularly polarized luminescence (CPL), showing a g in the range of 10. This simple structure represents one of the scarce examples of purely organic compounds combining both TPA and CPL responses, together with large values of molar absorptivity and fluorescence quantum yield with emission in the 500-600 nm. Self-assembly induced by introduction of a poor solvent allows for a spectacular shift of the emission into the near-infrared (NIR, 650-750 nm) by formation of well-defined rotationally displaced dimers. Therefore, we are here presenting a versatile platform whose optical properties can be simply tuned by self-assembly or by functionalization of the electron-deficient aromatic core of PDIs.

Citing Articles

A Chirally Locked Bis-perylene Diimide Macrocycle: Consequences for Chiral Self-Assembly and Circularly Polarized Luminescence.

Penty S, Orton G, Black D, Pal R, Zwijnenburg M, Barendt T J Am Chem Soc. 2024; 146(8):5470-5479.

PMID: 38355475 PMC: 10910538. DOI: 10.1021/jacs.3c13191.

The Pink Box: Exclusive Homochiral Aromatic Stacking in a Bis-perylene Diimide Macrocycle.

Penty S, Zwijnenburg M, Orton G, Stachelek P, Pal R, Xie Y J Am Chem Soc. 2022; 144(27):12290-12298.

PMID: 35763425 PMC: 9348826. DOI: 10.1021/jacs.2c03531.

Chiral Perylene Bisimide Dyes by Interlocked Arene Substituents in the Bay Area.

Renner R, Mahlmeister B, Anhalt O, Stolte M, Wurthner F Chemistry. 2021; 27(46):11997-12006.

PMID: 34133048 PMC: 8456824. DOI: 10.1002/chem.202101877.

Supramolecular Copolymerization of Bichromophoric Chiral and Achiral Perylenediimide Dyes.

Yonezawa S, Kawai T, Nakashima T Front Chem. 2021; 9:652703.

PMID: 33842436 PMC: 8032881. DOI: 10.3389/fchem.2021.652703.

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