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

Hüsniye Ardic Alidagi , Seda Çetindere

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.

Keywords

fluorenone, BODIPY, photophysical properties, small molecule

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.