Photoacoustic (PA) imaging has recently caught the attention of researchers due to its capability of generating high contrast images in deep tissue at a lower cost when compared with traditional diagnostic imaging. However, the field of PA imaging is lacking a sufficient library of molecular contrast agents that absorb within the biological transparency window (700-1300 nm). This presentation pertains to the design, synthesis and characterization of electron-rich dimethylaminophenyl and dimethylaminothiophene functionalized curcuminoid molecules, for application as PA contrast agents, whose absorbance is red-shifted toward the biological transparency window. A systematic approach was taken with respect to the design of a library of curcuminoid dyes whereby the terminal groups attached to the curcuminoid core were varied in an incremental fashion, i.e. a series of aryl and dimethylamino-aryl terminal groups were chosen based upon the phenyl, naptha and thiophene ring systems. The photophysical and electrochemical properties of each dye are presented using a combination of techniques including UV-Vis electronic absorption spectroscopy, steady-state and time-resolved fluorescence emission spectroscopy, and cyclic voltammetry. The electronic properties of these curcuminoid dyes are further probed by computational analysis using density functional theory methods. The absorbance characteristic and photoacoustic properties did not surpass previous curcuminoid compounds, the data collected provides vital structural and photo-physical information in improving the availability of efficient curcuminoid contrast agents for PA imaging.

Photophysical & photoacoustic properties of dimethylamino terminated curcuminoid dyes containing the phenyl, napthyl and thienyl π-spacers

254th National Meeting (2017)

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