Research Article

2-Naphthylthio Cyclotriphosphazene Derivatives: Synthesis, Characterization, Crystallographic and Fluorescence Properties

Volume: 8 Number: 2 May 31, 2021
EN

2-Naphthylthio Cyclotriphosphazene Derivatives: Synthesis, Characterization, Crystallographic and Fluorescence Properties

Abstract

In this study, new cyclotriphosphazene derivatives bearing 2-naphthylthio group were reported. The reactions of hexachlorocyclotriphosphazene (1) with 2-naphthalenethiol (2) were carried out with NaH base in tetrahydrofuran solution under inert (Ar) atmosphere in (1:2), (1:4) and (1:6) molar ratios. As a result of the reactions, bis geminal (3), tetrakis (4) and hexakis (5) 2-naphthylthio substituted cyclotriphosphazene derivatives formed and isolated. These new compounds were characterized with elemental analysis, mass (MALDI-TOF) analysis, 31P{H} and 1H NMR spectroscopies. The molecular structure of compound 3 was illuminated by single-crystal X-Ray diffraction technique. Furthermore, the fluorescence properties of the newly designed and synthesis compounds (3-5) were examined.

Keywords

References

  1. 1. Gleria M, Jaeger RD, editors. Applicative aspects of cyclophosphazenes. New York: Nova Science Publishers; 2004. 371 p.
  2. 2. Allcock HR. Chemistry and applications of polyphosphazenes [Internet]. Hoboken, N.J: Wiley-Interscience; 2003. 725 p. Available from: https://www.wiley.com/en-us/Chemistry+and+Applications+of+Polyphosphazenes-p-9780471443711
  3. 3. Bowers DJ, Wright BD, Scionti V, Schultz A, Panzner MJ, Twum EB, et al. Structure and Conformation of the Medium-Sized Chlorophosphazene Rings. Inorg Chem. 2014 Sep 2;53(17):8874–86.
  4. 4. Uslu A, Mutlu Balcı C, Yuksel F, Özcan E, Dural S, Beşli S. The investigation of thermosensitive properties of phosphazene derivatives bearing amino acid ester groups. J Mol Struct. 2017 May;1136:90–9.
  5. 5. Liu X, Breon JP, Chen C, Allcock HR. Substituent exchange reactions of trimeric and tetrameric aryloxycyclophosphazenes with sodium 2,2,2-trifluoroethoxide. Dalton Trans. 2012;41(7):2100–9.
  6. 6. Jiménez J, Callizo L, Serrano JL, Barberá J, Oriol L. Mixed-Substituent Cyclophosphazenes with Calamitic and Polycatenar Mesogens. Inorg Chem. 2017 Jul 17;56(14):7907–21.
  7. 7. Kumar D, Singh N, Keshav K, Elias AJ. Ring-Closing Metathesis Reactions of Terminal Alkene-Derived Cyclic Phosphazenes. Inorg Chem. 2011 Jan 3;50(1):250–60.
  8. 8. Mukundam V, Dhanunjayarao K, Mamidala R, Venkatasubbaiah K. Synthesis, characterization and aggregation induced enhanced emission properties of tetraaryl pyrazole decorated cyclophosphazenes. J Mater Chem C. 2016;4(16):3523–30.

Details

Primary Language

English

Subjects

Inorganic Chemistry

Journal Section

Research Article

Publication Date

May 31, 2021

Submission Date

January 8, 2021

Acceptance Date

March 29, 2021

Published in Issue

Year 2021 Volume: 8 Number: 2

APA
Mutlu Balcı, C. (2021). 2-Naphthylthio Cyclotriphosphazene Derivatives: Synthesis, Characterization, Crystallographic and Fluorescence Properties. Journal of the Turkish Chemical Society Section A: Chemistry, 8(2), 535-552. https://doi.org/10.18596/jotcsa.856600
AMA
1.Mutlu Balcı C. 2-Naphthylthio Cyclotriphosphazene Derivatives: Synthesis, Characterization, Crystallographic and Fluorescence Properties. JOTCSA. 2021;8(2):535-552. doi:10.18596/jotcsa.856600
Chicago
Mutlu Balcı, Ceylan. 2021. “2-Naphthylthio Cyclotriphosphazene Derivatives: Synthesis, Characterization, Crystallographic and Fluorescence Properties”. Journal of the Turkish Chemical Society Section A: Chemistry 8 (2): 535-52. https://doi.org/10.18596/jotcsa.856600.
EndNote
Mutlu Balcı C (May 1, 2021) 2-Naphthylthio Cyclotriphosphazene Derivatives: Synthesis, Characterization, Crystallographic and Fluorescence Properties. Journal of the Turkish Chemical Society Section A: Chemistry 8 2 535–552.
IEEE
[1]C. Mutlu Balcı, “2-Naphthylthio Cyclotriphosphazene Derivatives: Synthesis, Characterization, Crystallographic and Fluorescence Properties”, JOTCSA, vol. 8, no. 2, pp. 535–552, May 2021, doi: 10.18596/jotcsa.856600.
ISNAD
Mutlu Balcı, Ceylan. “2-Naphthylthio Cyclotriphosphazene Derivatives: Synthesis, Characterization, Crystallographic and Fluorescence Properties”. Journal of the Turkish Chemical Society Section A: Chemistry 8/2 (May 1, 2021): 535-552. https://doi.org/10.18596/jotcsa.856600.
JAMA
1.Mutlu Balcı C. 2-Naphthylthio Cyclotriphosphazene Derivatives: Synthesis, Characterization, Crystallographic and Fluorescence Properties. JOTCSA. 2021;8:535–552.
MLA
Mutlu Balcı, Ceylan. “2-Naphthylthio Cyclotriphosphazene Derivatives: Synthesis, Characterization, Crystallographic and Fluorescence Properties”. Journal of the Turkish Chemical Society Section A: Chemistry, vol. 8, no. 2, May 2021, pp. 535-52, doi:10.18596/jotcsa.856600.
Vancouver
1.Ceylan Mutlu Balcı. 2-Naphthylthio Cyclotriphosphazene Derivatives: Synthesis, Characterization, Crystallographic and Fluorescence Properties. JOTCSA. 2021 May 1;8(2):535-52. doi:10.18596/jotcsa.856600

Cited By