Synthesis of a Fluorophore with Improved Optical Brightness

Macduff Okuom, Mark Wilson, Jordan Groathouse, Junsik Lee, Dave Symonsbergen, Casey Gustafson, Mitch Trauernicht, Homar Barcena, Cassie Reicks, Sharmin Sikich, Raychelle Burks, Andrea Holmes

Chemistry Department, Doane College, Crete, USA.
Novel Chemical Solutions, Crete, USA.

DOI: 10.4236/ijoc.2013.34037                

Abstract

The synthesis and characterization of a novel fluorophore(1), with potential application as an optical brightener are reported. This compound was prepared by reacting 4,4-diaminostilbene-2,2-disulfonic acid with cyanuric chloride in the presence of Na₂CO₃ followed by the addition of trityl aniline. Solution and solid state fluorescence demonstrated a strong blue/purple emission centered at 450 nm. ¹H-NMR spectroscopy, mass spectrometry analysis, elemental analysis, and DOSY-NMR were used for the characterization of the fluorophore.

Keywords

Optical Brightener; Fluorophore; Diaminostilbene; Cyanuric Chloride; Optical Brightness

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	S. Dufresne, M. Gaultois and W. G. Skene, “Disodium 5,5’-Diamino-2,2’-ethylenedibenzenesulfonate Tetrahydrate,” Acta Crystallographica, Vol. 63, 2007, p. E63.
[2]	M. A. Hubbe, J. J. Pawlak and A. A. Koukoulas, “Paper’s Appearance: A Review,” BioResources, Vol. 3, No. 2, 2008, pp. 627-665.
[3]	I. D. Cohen, “Cosmetic Compositions Containing Optical Brighteners,” US Patent No: 09/320153, 1999.
[4]	US Food and Drug Administration, “Color Additives Inventory.” http://www.fda.gov/forindus try/coloradditives/coloradditiveinventories/ucm115641.htm
[5]	“Cosmetics Info.” http://www.cosmeticsinfo.org/products.php?category_id=7
[6]	P. de Hoog, P. Gamez, W. L. Driessen and J. Reedijk, “New Polydentate and Polynucleating N-Donor Ligands from Amines and 2,4,6-Trichloro-1,3,5-triazine,” Tetrahedron Letters, Vol. 43, No. 38, 2002, pp. 6783-6786. http://dx.doi.org/10.1016/S0040-4039(02)01498-3
[7]	“Proton Chemical Shifts.” http://www.chemwisc.edu/areas/reich/handouts/nmr-h/hdata{31}.gif
[8]	G. Morris, “Diffusion-Ordered Spectroscopy,” John Wiley & Sons Ltd., Chinchester, 2009.
[9]	D. Fujita, K. Suzuki, S. Sato and M. E. A. Yagi-Utsumi, “Protein Encapsulation within Synthetic Molecular Hosts,” Nature Commications, Vol. 3, 2012, p. 1093. http://dx.doi.org/10.1038/ncomms2093