Synthesis of Novel Diarylethenes Bearing Naphthalimide Moiety and Photochromic Fluorescence Behaviors

Year 2017, Volume: 4 Issue: 2, 501 - 516, 27.03.2017

Ersin Orhan

https://doi.org/10.18596/jotcsa.296370

Cited By: 2

Abstract

The objective of the research was to synthesise new
photo switchable photochromic fluorescence compounds. Starting from N-butyl-4-bromo-3-iodo-1,8-naphthalimide
new
compounds:
3,4-Bis(2-phenyl-5-methyl-4-thiazolyl)-N-butyl-1,8-naphthalimide 1O and 3,4-Bis(3,5-dimethyl-4-isoxazolyl)-N-butyl-1,8-naphthalimide
2O were prepared via two step Suzuki
coupling reaction of aryl boronic acid and esters, and their photochromic
fluorescence properties were investigated. Although all prepared bisaryl
naphthlimides were fluorescence due to the naphthlimide moiety, among them photochrome 1O
displayed photochromism. On exposure to ultraviolet light, the photochrome 1O showed a pale yellow to blue-green
colour change due to the formation of ring closed form 1C, which reversed to the ring opened form 1O on exposure to visible light. Conversion ratio and quantum
efficiency (from O to C form) for 1O
were also determined.

Additionally,
a solvent effect on the fluorescence properties of 1O and 2O was
investigated. Increase of solvent polarity results in a red shift (to longer
wavelengths) of the fluorescence emissions.

Keywords

Photochromism, Fluorescence, Diarylethene, Naphthalimide

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