Pyrene

Pyrene

Introduction

Pyrene, as a member of polycyclic aromatic hydrocarbons, mainly exists in the fractions of coal tar and asphalt, and has the characteristics of rich electrons, large ring conjugated, easy chemical modification, good crystallinity and so on. Pyrene fluorophore has been widely used in light-emitting diodes, bio-optoelectronic sensors and other research fields due to its high fluorescence efficiency, carrier mobility and excimer emission efficiency.

Fig.1 The chemical structure of pyrene

Application

• Organic light-emitting diodes (OLED): Pyrene derivatives have high optical transmittance in the visible region due to the abundance of π electrons. Thus, pyrene derivatives are widely used in organic photoelectric materials. According to the different molecular structure, pyrene organic photoelectric materials can be divided into three types: small molecular derivatives, dendritic macromolecules and star oligomers and polymer materials. Especially, electrogenerated chemiluminescence (ECL) has also promising applications in OLEDs, which are currently used in long-lived and highly efficient color displays, its luminescence intensity of ELC can be increased by 5 times after the modification of pyrene ^[1].

Fig.2 Electrochemical luminescence of pyrene derivatives ^[1]

• Photochemical sensor: Pyrene has been widely used in photochemical sensors due to its photophysical properties such as high quantum yield and luminescence intensity, long phosphorescence lifetime and so on. Raihana ^[2] has synthesized a novel pyrene based fluorescent sensor for selective “turn on”, the sensor also exhibited very low cytotoxicity and strong fluorescence emission in living cells, indicating its potential applicability as a novel chemical sensor for selective detection of Ni²⁺ ions in biological environment also.

Fig.3 Plausible mechanism of Pyr-1complexation with Ni²⁺ ion and removal of Ni²⁺ by EDTA.

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References

• Yeon Ok Lee.; et al. Enhanced Electrogenerated Chemiluminescence of Phenylethynylpyrene Derivatives: Use of Weakly Electron-Donating Group as a Substituent. J. Org. Chem, 2012, 77, 11007−11013.
• Khan, Raihana Imran.; et al. Design and one-pot synthesis of a novel pyrene based fluorescent sensor for selective "turn on", naked eye detection of Ni²⁺ ions, and live cell imaging. Sensors and Actuators B: Chemical, 2018 (266): 429-437.