Photophysical and Photoacoustic Properties of Quadrupolar Borondifluoride Curcuminoid Dyes

Overview

Journal Chemistry

Specialty Chemistry

Date 2017 Nov 18

PMID 29149546

Citations 6

Authors

Stephanie Bellinger

Maryam Hatamimoslehabadi

Seema Bag

Farha Mithila

Jeffrey La

Mathieu Frenette

Samir Laoui

David J Szalda

Chandra Yelleswarapu

Jonathan Rochford

Affiliations

Soon will be listed here.

Abstract

The synthesis and characterization of a series of donor-π-acceptor-π-donor (D-A-D) curcuminoid molecules is presented herein that incorporates π-extended aryl and electron-donating amino terminal functionalization. Computational evaluation shows these molecules possess quadrupolar character with the lowest energy transitions displaying high molar extinction coefficients with broad tunability through manipulation of terminal donating groups. Consistent with their quadrupolar nature, these molecules show varying degrees of solvatochromic behavior in both their absorption and emission spectra, which has been analyzed by Lippert-Mataga and Kamlet-Taft analysis. Photophysical and photoacoustic (PA) properties of these molecules have been investigated by the optical photoacoustic z-scan (OPAZ) method. Selected curcuminoid molecules display nonlinear behavior at a high laser fluence through excited state absorption that translates to the production of an enhanced photoacoustic emission. A relative comparison of "molar PA emission" is also presented with the crystal violet linear optical absorbing/linear PA emitting system being utilized as a standard reference material for OPAZ experiments. Furthermore, PA tomography experiments are presented to illustrate the enhanced PA contrast obtainable via an excited state absorption.

Citing Articles

Photoluminescent Properties and Mechanism of Novel Cyanine-Borondifluoride Curcuminoid Hybrids as Red-to-Near Infrared and Endoplasmic Reticulum-Targeting Dyes.

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High Yield Synthesis of Curcumin and Symmetric Curcuminoids: A "Click" and "Unclick" Chemistry Approach.

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Recent development of near-infrared photoacoustic probes based on small-molecule organic dye.

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Photophysical and Photoacoustic Properties of π-Extended Curcumin Dyes. Effects of the Terminal Dimethylamino Electron-donor and the Bridging Aryl Ring.

Borg R, Hatamimoslehabadi M, Bellinger S, La J, Mithila F, Yelleswarapu C Photochem Photobiol. 2018; 95(1):280-292.

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Molecular Photoacoustic Contrast Agents: Design Principles & Applications.

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