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Synthesis and Characterization of Fluorenone Based Small Molecule and Investigation of Its Photophysical Properties

Year 2022, Volume: 1 Issue: 1, 41 - 46, 30.01.2022

Abstract

A fluorenone-based small molecule consisting of central 2,7-bis(ethynyl)-9-fluorenone core and BODIPY units at both sides (3) has been developed through the palladium/copper-catalyzed Sonogashira coupling reactions. The newly synthesized molecule was characterized by Fourier transform infrared (FT-IR), proton/carbon nuclear magnetic resonance (1H/13C NMR), mass (MALDI-TOF), and elemental analysis. The photophysical properties of the new compound and its precursor were investigated by ultraviolet-visible (UV-Vis) and fluorescence spectroscopy techniques.

References

  • [1] Mastral A. M., Callén M. S. (2000). A Review on Polycyclic Aromatic Hydrocarbon (PAH) Emissions from Energy Generation. Environmental Science and Technology; 34:3051–3057.
  • [2] Cerniglia C. E. (1992). Biodegradation of polycyclic aromatic hydrocarbons. Biodegradation; 3:351–368.
  • [3] Sonar P., Ha T-J., Dodabalapur A. (2013). A fluorenone based low band gap solutionprocessable copolymer for air stable and high mobilityorganic field effect transistors. Chemical Communications; 49:1588—1590.
  • [4] Gudeika D., Nasiri S., Mahmoudi M., Dabrovolskas K., Navozenko O. M., Yashchuk V. V. (2021). Design, synthesis and structure-property relationship of fluorenone-based derivatives for fluorescent OLEDs”, Molecular Crystals and Liquid Crystals; 718:1–15.
  • [5] Ghosh I., Mukhopadhyay A., Koner A. L., Samanta S., Nau W. M., Moorthy J. N. (2014). Excited-state properties of fluorenones: influence of substituents, solvent and macrocyclic encapsulation. Physical Chemistry Chemical Physics; 16: 16436-16445.
  • [6] Huang T.-H., Wang Y.-H., Kang Z.-H., Yao J., Lu R., Zhang H-Z. (2014). Investigation on Photophysical Properties of D–p–A–p–D-Type Fluorenone-Based Linear Conjugated Oligomers by Using Femtosecond Transient Absorption Spectroscopy. Photochemistry and Photobiology; 90:29–34.
  • [7] Zhou Y., Chen Y.Z., Cao J.H., Yang Q.Z., Wu L. Z., Tung C.H. (2015). Dicyanoborondiketonate dyes: synthesis, photophysical properties and bioimaging. Dyes and Pigments; 112:162–169.
  • [8] Zhao J., Xu K., Yang W., Wang Z., Zhong F. (2015). The triplet excited state of Bodipy:formation, modulation and application. Chemical Society Reviews; 44:8904–8939.
  • [9] Lu H., Mac K. J., Yang Y., Shen Z. (2014). Structural modification strategies for the rational design of red/NIR region BODIPYs. Chemical Society Reviews; 43:4778–823.
  • [10] Ardic Alidagi H., Cetindere S. (2021). A Novel Conjugated Pyrene-BODIPY Dyad: Synthesis, Characterization and Properties. Journal of Turkish Chemical Society Section A; 8:313-322.
  • [11] Tian Z., Yang X., Liu B., Zhong D., Zhou G. (2019). Photophysical properties and optical power limiting ability of Pt(II)polyynes bearing fluorene-type ligands with ethynyl units at different positions. Journal of Organometallic Chemistry; 895:28-36.
  • [12] Li B., Liu Y., Tao Y., Wang Y., Miao X., Cheng X., Deng W. (2020). Concentration-Dependent Conformational Isomerization of Fluorenone-Based Polycatenar in 2D Polymorphic Self-Assembly. The Journal of Physical Chemistry C; 124:25396−25402.
  • [13] Xu F., Yuan M-S., Wang W., Du X., Wang H., Li N., Yu R., Du Z., Wang J. (2016). Symmetric and unsymmetric thienyl-substituted fluorenone dyes: static excimer-induced emissionenhancement. The Royal Society of Chemistry Advances; 16:76401–76408.
Year 2022, Volume: 1 Issue: 1, 41 - 46, 30.01.2022

Abstract

References

  • [1] Mastral A. M., Callén M. S. (2000). A Review on Polycyclic Aromatic Hydrocarbon (PAH) Emissions from Energy Generation. Environmental Science and Technology; 34:3051–3057.
  • [2] Cerniglia C. E. (1992). Biodegradation of polycyclic aromatic hydrocarbons. Biodegradation; 3:351–368.
  • [3] Sonar P., Ha T-J., Dodabalapur A. (2013). A fluorenone based low band gap solutionprocessable copolymer for air stable and high mobilityorganic field effect transistors. Chemical Communications; 49:1588—1590.
  • [4] Gudeika D., Nasiri S., Mahmoudi M., Dabrovolskas K., Navozenko O. M., Yashchuk V. V. (2021). Design, synthesis and structure-property relationship of fluorenone-based derivatives for fluorescent OLEDs”, Molecular Crystals and Liquid Crystals; 718:1–15.
  • [5] Ghosh I., Mukhopadhyay A., Koner A. L., Samanta S., Nau W. M., Moorthy J. N. (2014). Excited-state properties of fluorenones: influence of substituents, solvent and macrocyclic encapsulation. Physical Chemistry Chemical Physics; 16: 16436-16445.
  • [6] Huang T.-H., Wang Y.-H., Kang Z.-H., Yao J., Lu R., Zhang H-Z. (2014). Investigation on Photophysical Properties of D–p–A–p–D-Type Fluorenone-Based Linear Conjugated Oligomers by Using Femtosecond Transient Absorption Spectroscopy. Photochemistry and Photobiology; 90:29–34.
  • [7] Zhou Y., Chen Y.Z., Cao J.H., Yang Q.Z., Wu L. Z., Tung C.H. (2015). Dicyanoborondiketonate dyes: synthesis, photophysical properties and bioimaging. Dyes and Pigments; 112:162–169.
  • [8] Zhao J., Xu K., Yang W., Wang Z., Zhong F. (2015). The triplet excited state of Bodipy:formation, modulation and application. Chemical Society Reviews; 44:8904–8939.
  • [9] Lu H., Mac K. J., Yang Y., Shen Z. (2014). Structural modification strategies for the rational design of red/NIR region BODIPYs. Chemical Society Reviews; 43:4778–823.
  • [10] Ardic Alidagi H., Cetindere S. (2021). A Novel Conjugated Pyrene-BODIPY Dyad: Synthesis, Characterization and Properties. Journal of Turkish Chemical Society Section A; 8:313-322.
  • [11] Tian Z., Yang X., Liu B., Zhong D., Zhou G. (2019). Photophysical properties and optical power limiting ability of Pt(II)polyynes bearing fluorene-type ligands with ethynyl units at different positions. Journal of Organometallic Chemistry; 895:28-36.
  • [12] Li B., Liu Y., Tao Y., Wang Y., Miao X., Cheng X., Deng W. (2020). Concentration-Dependent Conformational Isomerization of Fluorenone-Based Polycatenar in 2D Polymorphic Self-Assembly. The Journal of Physical Chemistry C; 124:25396−25402.
  • [13] Xu F., Yuan M-S., Wang W., Du X., Wang H., Li N., Yu R., Du Z., Wang J. (2016). Symmetric and unsymmetric thienyl-substituted fluorenone dyes: static excimer-induced emissionenhancement. The Royal Society of Chemistry Advances; 16:76401–76408.
There are 13 citations in total.

Details

Primary Language English
Journal Section Research Articles
Authors

Hüsniye Ardic Alidagi

Seda Çetindere

Publication Date January 30, 2022
Published in Issue Year 2022 Volume: 1 Issue: 1

Cite

APA Ardic Alidagi, H., & Çetindere, S. (2022). Synthesis and Characterization of Fluorenone Based Small Molecule and Investigation of Its Photophysical Properties. Cukurova University Journal of Natural and Applied Sciences, 1(1), 41-46.
AMA Ardic Alidagi H, Çetindere S. Synthesis and Characterization of Fluorenone Based Small Molecule and Investigation of Its Photophysical Properties. Cukurova University Journal of Natural and Applied Sciences. January 2022;1(1):41-46.
Chicago Ardic Alidagi, Hüsniye, and Seda Çetindere. “Synthesis and Characterization of Fluorenone Based Small Molecule and Investigation of Its Photophysical Properties”. Cukurova University Journal of Natural and Applied Sciences 1, no. 1 (January 2022): 41-46.
EndNote Ardic Alidagi H, Çetindere S (January 1, 2022) Synthesis and Characterization of Fluorenone Based Small Molecule and Investigation of Its Photophysical Properties. Cukurova University Journal of Natural and Applied Sciences 1 1 41–46.
IEEE H. Ardic Alidagi and S. Çetindere, “Synthesis and Characterization of Fluorenone Based Small Molecule and Investigation of Its Photophysical Properties”, Cukurova University Journal of Natural and Applied Sciences, vol. 1, no. 1, pp. 41–46, 2022.
ISNAD Ardic Alidagi, Hüsniye - Çetindere, Seda. “Synthesis and Characterization of Fluorenone Based Small Molecule and Investigation of Its Photophysical Properties”. Cukurova University Journal of Natural and Applied Sciences 1/1 (January 2022), 41-46.
JAMA Ardic Alidagi H, Çetindere S. Synthesis and Characterization of Fluorenone Based Small Molecule and Investigation of Its Photophysical Properties. Cukurova University Journal of Natural and Applied Sciences. 2022;1:41–46.
MLA Ardic Alidagi, Hüsniye and Seda Çetindere. “Synthesis and Characterization of Fluorenone Based Small Molecule and Investigation of Its Photophysical Properties”. Cukurova University Journal of Natural and Applied Sciences, vol. 1, no. 1, 2022, pp. 41-46.
Vancouver Ardic Alidagi H, Çetindere S. Synthesis and Characterization of Fluorenone Based Small Molecule and Investigation of Its Photophysical Properties. Cukurova University Journal of Natural and Applied Sciences. 2022;1(1):41-6.