Development of Circularly Polarized Luminescence (CPL) Peptides Containing Pyrenylalanines and 2-Aminoisobutyric Acid

Yuki Mimura,Yuki Motomura,Mizuki Kitamatsu,Yoshitane Imai

doi:10.3390/pr8121550

Yuki Mimura, Yuki Motomura + Show 2 more

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https://doi.org/10.3390/pr8121550

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Journal: Processes	Publication Date: Nov 27, 2020
Citations: 3	License type: CC BY 4.0

Affiliation: Kindai University

Abstract

Chiral organic and organometallic luminophores that possess circularly polarized luminescence (CPL) properties in the near-ultraviolet to near-infrared region have several useful applications. However, the CPL properties are subject to inherent factors of the compounds; to date, studies on the CPL properties influenced by amino acids and peptides are scarce. Consequently, we developed peptide-pyrene organic luminophores exhibiting various CPL properties. It is conceivable that the peptide-pyrene organic luminophores can be obtained as aggregates when dissolved in a solution. It is also possible that the formation of aggregates makes it difficult to accurately examine the CPL of the peptide in the solution. This study showed that the introduction of sterically hindered 2-aminoisobutyric acid (Aib) units into the peptide backbone inhibits aggregate formation. The resulting luminophores exhibit CPL properties owing to the presence of pyrene units. The results of this study can form a basis for the design of future materials that use peptide-pyrene organic luminophores.

Highlights

It has been recently proposed that chiral organic and organometallic luminophores with circularly polarized luminescence (CPL) properties in the near-ultraviolet to near-infrared region can be employed in a variety of useful applications, such as 3D displays and photonic devices [1,2,3,4,5,6,7,8,9,10,11].very few studies have investigated the effects of amino acids and peptides on the CPL properties
The compounds bearing no Aib unit exhibited trace aggregate formation whenfour fourpyrene pyreneunits unitswere were introduced introduced into it it was observed that formation when into the thepeptide
When the Gly unitthe wasGly introduced, aggregatethe formation was formation was observed in both chloroform and ethanol solutions when four pyrene units were observed in both chloroform and ethanol solutions when four pyrene units were introduced

Summary

Introduction

It has been recently proposed that chiral organic and organometallic luminophores with circularly polarized luminescence (CPL) properties in the near-ultraviolet to near-infrared region can be employed in a variety of useful applications, such as 3D displays and photonic devices (e.g., organic LEDs) [1,2,3,4,5,6,7,8,9,10,11].very few studies have investigated the effects of amino acids and peptides on the CPL properties. It has been recently proposed that chiral organic and organometallic luminophores with circularly polarized luminescence (CPL) properties in the near-ultraviolet to near-infrared region can be employed in a variety of useful applications, such as 3D displays and photonic devices (e.g., organic LEDs) [1,2,3,4,5,6,7,8,9,10,11]. We previously investigated peptide-pyrene organic luminophores exhibiting CPL properties where no aggregate formation took place between pyrene units and found that chiral oligopeptides with multiple pyrene units exhibit a strong CPL signal from the excimers. It is difficult to purify a peptide containing five or more pyrene moieties due to such aggregate formation. To address this issue, we investigate various methods to prevent the formation of aggregates.

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