Journals / Journal of the Turkish Chemical Society Section A: Chemistry / 2017 / Cilt: 4 - Sayı: 2

Synthesis of Novel Diarylethenes Bearing Naphthalimide Moiety and Photochromic Fluorescence Behaviors

Pages
501–516
Publication Date
2017-03-27
DOI
—
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Increase of solvent polarity results in a red shift (to longer wavelengths) of the fluorescence emissions.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:The objective of the research was to synthesise new photo switchable photochromic fluorescence compounds.
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Key Findings & Data: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.
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Conclusion & Impact:Increase of solvent polarity results in a red shift (to longer wavelengths) of the fluorescence emissions.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Photochromism · Fluorescence · Diarylethene

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.

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Cite This Article

ORHAN, E. (2017). Synthesis of Novel Diarylethenes Bearing Naphthalimide Moiety and Photochromic Fluorescence Behaviors. Journal of the Turkish Chemical Society Section A: Chemistry, Cilt: 4 - Sayı: 2, 501–516. https://ajindex.com/articles/781547

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References (15)

  1. Tsujioka T, Irie M. Electrical functions of photochromic molecules. Journal of Photochemistry and Photobiology C: Photochemistry Reviews. 2010 Mar;11(1):1–14
  2. Rau H, Durr H. Photochromism: molecules and systems. Photochromism, Molecules and Systems. 1990;165–192
  3. Irie M. Diarylethenes for Memories and Switches. Chemical Reviews. 2000 May;100(5):1685–716
  4. Köse M, Orhan E. Comparison of photochromic properties and thermal stabilities of fulgide, fulgimide, and benzimidazole[1,2-a]pyrrolidine-2-one derivatives. Turk J Chem. 2009;33:579–88
  5. Kose M, Orhan E, Büyükgüngör O. Synthesis of novel photochromic methyl cyanoacetate-condensed fulgide derivatives. Journal of Photochemistry and Photobiology A: Chemistry. 2007 May;188(2–3):358–63
  6. Kose M, Orhan E. Studies on photochromic benzimidazol[1,2a]pyrrolidin-2-ones from the condensation of 2-methyl-3-benzothienylethylidene-(isopropylidene)succinic anhydride with 1,2-diaminobenzenes. Journal of Photochemistry and Photobiology A: Chemistry. 2006 Jan;177(2–3):170–6
  7. Matsuda K, Irie M. Diarylethene as a photoswitching unit. Journal of Photochemistry and Photobiology C: Photochemistry Reviews. 2004 Oct;5(2):169–82
  8. Krayushkin M, Ivanov S, Martynkin AY, Lichitsky B, Dudinov A, Uzhinov B. Photochromic dihetarylethenes
  9. Synthesis of bis (thienylazoles), photochromic analogs of diarylethenes. Russian Chemical Bulletin. 2001;50(1):116–121
  10. Nakashima T, Atsumi K, Kawai S, Nakagawa T, Hasegawa Y, Kawai T. Photochromism of Thiazole-Containing Triangle Terarylenes. European Journal of Organic Chemistry. 2007 Jul;2007(19):3212–8
  11. Orhan E, Gundogdu L, Kose M, Yokoyama Y. Synthesis and photochromic properties of 4,5-bisaryl-3(2H)-pyridazinones. Journal of Photochemistry and Photobiology A: Chemistry. 2016 Jan;314:164–70
  12. Meng X, Zhu W, Zhang Q, Feng Y, Tan W, Tian H. Novel Bisthienylethenes Containing Naphthalimide as the Center Ethene Bridge: Photochromism and Solvatochromism for Combined NOR and INHIBIT Logic Gates. The Journal of Physical Chemistry B. 2008 Dec 11;112(49):15636–45
  13. Tian H, Wang S. Photochromic bisthienylethene as multi-function switches. Chem Commun. 2007;(8):781–92
  14. Kanazawa R, Nakashima T, Kawai T. Photophysical Properties of a Terarylene Photoswitch with a Donor–Acceptor Conjugated Bridging Unit. The Journal of Physical Chemistry A. 2017 Mar 2;121(8):1638–46
  15. Cheng H-B, Tan X, Pang M-L. Near-Infrared Photochromic Diarylethenes Based on the Changes in the π-Conj