Journals / Turkish Journal of Chemistry / 2020 / Cilt: 44 - Sayı: 1

Pyrene-BODIPY-substituted novel water-soluble cyclotriphosphazenes: synthesis, characterization, and photophysical properties

Pages
1–14
Publication Date
2022-11-04
DOI
—
🏛️Bibliographic metadata and full text access for this article are provided via DergiPark.
DergiPark Record ↗
✨

AI Summary & Key Takeaways

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

It was found that the targetcompounds were soluble in water and could be potential candidates as water-soluble fluorescent dyes for the desired applications.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:In the present work, pyrene-boron-dipyrromethene (BODIPY)-substituted novel water-soluble cyclotriphosphazene derivatives (6 and 7) were synthesized by click reactions between a cyclotriphosphazene derivative with ahydrophilic glycol side group (2) and BODIPYs (4 and 5).
📊
Key Findings & Data:All of the new compounds (2, 6, and 7) were characterizedby Fourier-transform infrared and nuclear magnetic resonance spectroscopy, as well as mass spectrometry and elementalanalysis.
💡
Conclusion & Impact:It was found that the targetcompounds were soluble in water and could be potential candidates as water-soluble fluorescent dyes for the desired applications.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters

Abstract

In the present work, pyrene-boron-dipyrromethene (BODIPY)-substituted novel water-soluble cyclotriphosphazene derivatives (6 and 7) were synthesized by click reactions between a cyclotriphosphazene derivative with ahydrophilic glycol side group (2) and BODIPYs (4 and 5). All of the new compounds (2, 6, and 7) were characterizedby Fourier-transform infrared and nuclear magnetic resonance spectroscopy, as well as mass spectrometry and elementalanalysis. The photophysical properties of the BODIPY-substituted cyclotriphosphazenes (6 and 7) were investigatedby UV-Vis and fluorescence emission spectroscopy in water and water/solvent mixtures. It was found that the targetcompounds were soluble in water and could be potential candidates as water-soluble fluorescent dyes for the desired applications.

🔖

Cite This Article

KILIÇ, A., YEŞİLOT, S., ÇETİNDERE, S. (2022). Pyrene-BODIPY-substituted novel water-soluble cyclotriphosphazenes: synthesis, characterization, and photophysical properties. Turkish Journal of Chemistry, Cilt: 44 - Sayı: 1, 1–14. https://ajindex.com/articles/601592

📄 Full Text PDF Viewer

📄

PDF görüntüleyici hazırlanıyor...

References (13)

  1. Görl D, Zhang X, Würthner F. Molecular assemblies of perylene bisimide dyes in water. Angewandte Chemie International Edition 2012
  2. 51 (26): 6328-6348. doi: 10.1002/anie.201108690 2. Loudet A, Burgess K. BODIPY dyes and their derivatives: syntheses and spectroscopic properties. Chemical Reviews 2007
  3. 107 (11): 4891-4932. doi: 10.1021/cr078381n 3. Ziessel R, Ulrich G, Harriman A. The chemistry of BODIPY: a new El Dorado for fluorescence tools. New Journal of Chemistry 2007
  4. 31 (4): 496-501. doi: 10.1039/b617972j 4. Ulrich G, Ziessel R, Harriman A. The chemistry of fluorescent BODIPY dyes: versatility unsurpassed. Angewandte Chemie International Edition 2008
  5. 47 (7): 1184-1201. doi: 10.1002/anie.200702070 5. Bricks JL, Kovalchuk A, Trieflinger C, Nofz M, Büschel M et al. On the development of sensor molecules that display Fe III -amplified fluorescence. Journal of the American Chemical Society 2005
  6. 127 (39): 13522-13529. doi: 10.1021/ja050652t 6. Qin WW, Baruah M, Stefan A, Auweraer MV, Boens N. Photophysical properties of BODIPY-derived hydroxyaryl fluorescent pH probes in solution. European Journal of Chemical Physics and Physical Chemistry 2005
  7. 6 (11): 2343-2351. doi: 10.1002/cphc.200500341 7. Wagner RW, Lindsey JS. Boron-dipyrromethene dyes for incorporation in synthetic multi-pigment light-harvesting arrays. Pure and Applied Chemistry 1996
  8. 68 (7): 1373-1380. doi: 10.1351/pac199668071373 8. Rurack K, Kollmannsberger M, Daub J. Molecular switching in the near infrared (NIR) with a functionalized boron-dipyrromethene dye. Angewandte Chemie International Edition 2001
  9. 40 (2): 385-387. doi: 10.1002/1521- 3773(20010119)40:2 3.0.CO
  10. F 9. Gabe Y, Urano Y, Kikuchi K, Kojima H, Nagano T. Highly sensitive fluorescence probes for nitric oxide based on boron dipyrromethene chromophore rational design of potentially useful bioimaging fluorescence probe. Journal of the American Chemical Society 2004
  11. 126 (10): 3357-3367. doi: 10.1021/ja037944j 10. Guo B, Peng X, Cui A, Wu Y, Tian M et al. Synthesis and spectral properties of new boron dipyrromethene dyes. Dyes and Pigments 2007
  12. 73 (2): 206-210. doi: 10.1016/j.dyepig.2005.11.007 11. Coskun A, Akkaya EU. Difluorobora-s-diazaindacene dyes as highly selective dosimetric reagents for fluoride anions. Tetrahedron Letters 2004
  13. 45 (25): 4947-4949. doi: 10.1016/j.tetlet.2004.04.130 12. Fan G, Yang L, Chen Z. Water-soluble BODIPY and aza-BODIPY dyes: synthetic progress and applications. Frontiers of Chemical Science an