(Z)-3-(Dicyanomethylene)-4-((5-fluoro-3,3-dimethyl-1-(3-phenylpropyl)-3H-indol-1-ium-2-yl) methylene)-2-(((E)-5-fluoro-3,3-dimethyl-1-(3-phenylpropyl)indolin-2-ylidene)methyl) cyclobut-1-en-1-olate

Author:

Casa Stefanie1ORCID,Ersoy Ozmen Guliz1,Henary Maged12ORCID

Affiliation:

1. Department of Chemistry, Petit Science Center, Georgia State University, 100 Piedmont Avenue SE, Atlanta, GA 30303, USA

2. Center for Diagnostics and Therapeutics, Petit Science Center, Georgia State University, 100 Piedmont Avenue SE, Atlanta, GA 30303, USA

Abstract

Recent literature on this topic highlights the significance of adding malononitrile moiety and halogen substituents to the squaraine scaffold to create redshifted fluorophores into the near-infrared optical region. Herein, a redshifted hydrophobic squaraine dye is synthesized via a three-step pathway. The reported dye is characterized by spectroscopic techniques, such as 1H NMR, 19F NMR, 13C NMR, and high-resolution mass spectroscopy. Optical properties are also reported using absorbance and fluorescence studies. The hydrophobicity of the dye was studied with absorbance and fluorescence spectroscopy in water–methanol mixtures and showed J-aggregates as the water concentration increased. Density functional theory calculations were conducted to assess its electron delocalization as well as observe the three-dimensional geometry of the dye as a result of the dicyanomethylene modification and the two bulky phenyl groups.

Funder

NIH/NIBIB

Brains and Behavior Seed

Health Innovation Platform

Georgia Research Alliance Venture

Publisher

MDPI AG

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

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