Bimolecular Interactions Between Graphene Oxide and a New Aza-BODIPY Derivative

Abstract

Fluorescent dyes are optical devices which are commonly used in medical and technical applications. Graphene-oxide, on the other hand, is a unique structure in nanotechnology with its oxygen-containing functional groups, high solubility, optical, electronic and thermal properties. Here we report photophysical properties of a newly synthesized fluorescent aza-BODIPY dye and dye-graphene oxide (GO) composite in aqueous media. Quantum yields were determined in both ethanol and chloroform medias according to Perker-Rees equation. Also quenching mechanism was discussed in the light of Stern-Volmer parameters.

Keywords

• azabodipy
• graphene oxide
• fluorescent
• dye

Supporting Institution

Atatürk University

Project Number

FHD-2017-6181

References

1. Aydın BM, Acar M, Arık M, Onganer Y, 2009. The fluorescence resonance energy transfer between dye compounds in micellar media. Dyes and Pigments, 81:156-160.
2. Balapanuru J, Yang JX, Xiao S, Bao Q, Jahan M, Polavarapu L, Loh KP, 2010. A graphene oxide–organic dye ionic complex with dna‐sensing and optical‐limiting properties. Angewandte Chemie International Edition, 49(37):6549-6553.
3. Brouwer AM, 2011. Standards for photoluminescence quantum yield measurements in solution. Pure and Applied Chemistry, 83(12):2213-2228.
4. Chen D, Zhong Z, Ma Q, Shao J, Huang W, Dong X, 2020. Aza-BODIPY-Based nanomedicines in cancer phototheranostics. ACS Applied Materials & Interfaces, 12:26914-26925.
5. Dimiev AM, Tour JM, 2014. Mechanism of graphene oxide formation. ACS nano, 8(3):3060-3068.
6. Dreyer DR, Park S, Bielawski CW, Ruoff RS, 2010. The chemistry of graphene oxide. Chemical Society Reviews, 39(1):228-240.
7. Gorman A, Killoran J, O'Shea C, Kenna T, Gallagher WM, O'Shea DF, 2004. In vitro demonstration of the heavy-atom effect for photodynamictherapy. Journal of the American Chemical Society, 126(34):10619-10631.
8. Hall MJ, McDonnell SO, Killoran J, O'Shea DF, 2005. A modular synthesis of unsymmetrical tetraarylazadipyrromethenes. The Journal of Organic Chemistry, 70(14):5571-5578.

9. Killoran J, Allen L, Gallagher JF, Gallagher WM, Donal FO, 2002. Synthesis of BF2 chelates of tetraarylazadipyrromethenes and evidence for their photodynamic therapeutic behaviour. Chemical Communications, 17:1862-1863.
10. Lakowicz JR, 1983. Principles of Fluorescence Spectroscopy. Plenium Press, pp. 278-285, New York-USA
11. Li L, Li W, Wang L, Tang H, Cao D, Ran X, 2020. Pyrrolopyrrole aza-BODIPY dyes for ultrasensitive and highly selective biogenic diamine detection. Sensors & Actuators: B. Chemical 312, 127953:1-10.
12. Loudet A, Burgess K, 2007. Bodipy dyes and their derivatives: syntheses and spectroscopic properties. Chemical Reviews, 107(11):4891-4932.
13. Lu H, Mack J, Yang Y, Shen Z, 2014. Structural modification strategies for the rational design of red/NIR region bodipys. Chemical Society Reviews, 43(13):4778-4823.
14. Narayanan R, Deepa M, Srivastava AK, 2012. Nanoscale connectivity in a TiO2/CdSe quantum dots/functionalized graphene oxide nanosheets/Au nanoparticles composite for enhanced photoelectrochemical solar cell performance. Physical Chemistry Chemical Physics, 14(2):767-778.
15. Petersen S, Glyvradal M, Boggild P, Hu W, Feidenhans'l R, Laursen BW, 2012. Graphene oxide as a monoatomic blocking layer. ACS Nano, 6(9):8022-8029.
16. Ramesha GK, Kumara AV, Muralidhara HB, Sampath S, 2011. Graphene and graphene oxide as effective adsorbents toward anionic and cationic dyes. Journal of Colloid and Interface Science, 361(1):270-277.
17. Zhang LL, Zhao X, Stoller MD, Zhu Y, Ji H, Murali S, Ruoff RS, 2012. Highly conductive and porous activated reduced graphene oxide films for highpower supercapacitors. Nano Letters, 12(4):1806-1812.
18. Zhao Y, Li K, He Z, Zhang Y, Zhao Y, Zhang H, Miao Z, 2016. Investigation on fluorescence quenching mechanism of perylene diimide dyes by graphene oxide. Molecules, 21, (1642):1-7.
19. Zhu X, Zhu Y, Murali S, Stoller MD, Ruoff RS, 2011. Nanostructured reduced graphene oxide/Fe2O3 composite as a high-performance anode material for lithium ion batteries. ACS Nano, 5(4):3333-3338.
20. Ziessel R, Goze C, Ulrich G, 2007. Design and synthesis of alkyne-substituted boron in dipyrromethene frameworks. Synthesis, 06:936-949.
21. Zuo J, Pan H, Zhang Y, Chen Y, Wang H, Ren XK, Chen Z, 2020. Near-infrared fluorescent amphiphilic Aza-BODIPY dye: Synthesis, solvatochromic properties, and selective detection of Cu2+. Dyes and Pigments, 183,108714:1-7.