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. 2017 May 30:12:1177390117711938.
doi: 10.1177/1177390117711938. eCollection 2017.

Synthesis and Optical Properties of Pentamethine Cyanine Dyes With Carboxylic Acid Moieties

Tyler L Dost  1 , Michael T Gressel  1 , Maged Henary  1
Affiliations

Synthesis and Optical Properties of Pentamethine Cyanine Dyes With Carboxylic Acid Moieties

Tyler L Dost et al. Anal Chem Insights. .

Abstract

Cyanine dyes possessing carboxylic acid groups have been used in many different fields of study. The acid groups can act as handles for bioconjugation or as metal chelators. Several pentamethine cyanine dyes with propionic acid handles were synthesized and their optical properties were studied to determine their usefulness as fluorescent probes. The optical properties studies performed include the absorbance and emission maxima values as well as the calculation of quantum yield and molecular brightness levels. Molecular models were also calculated to help analyze the dyes' behavior and were compared with similar dyes with varying alkyl chain lengths replacing the acid moieties.

Keywords: Carboxylic acid; cyanine; optical properties; pentamethine.

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Conflict of interest statement

DECLARATION OF CONFLICTING INTERESTS: The author(s) declared no potential conflicts of interest with respect to the research, authorship, and/or publication of this article. Disclosures and Ethics As a requirement of publication author(s) have provided to the publisher signed confirmation of compliance with legal and ethical obligations including, but not limited to, the following: authorship and contributorship, conflicts of interest, privacy and confidentiality and (where applicable) protection of human and animal research subjects. The authors have read and confirmed their agreement with the ICMJE authorship and conflict of interest criteria. The authors have also confirmed that this article is unique and not under consideration or published in any other publication, and that they have permission from rights holders to reproduce any copyrighted material. Any disclosures are made in this section. The external blind peer reviewers report no conflicts of interest.

Figures

Scheme 1
Scheme 1
The synthetic route used to obtain compounds 4a–f from their corresponding phenylhydrazines 1.
Figure 1
Figure 1
The absorbance spectra and r2 spectra and value for each dilution of compound 4a.
Figure 2
Figure 2
The highest occupied molecular orbital (HOMO)/lowest unoccupied molecular orbital (LUMO) electron cloud distribution for compound 4c. The bromine atom at the meso-position points up instead of down.
Figure 3
Figure 3
The minimized structures of compounds with varying N-groups: methyl (top), butyl (middle), and propionic acid (bottom) to visualize the puckering displayed by the acid compounds.
Figure 4
Figure 4
A minimized calculated structure comparison of 2 pentamethine cyanine dyes that show the difference in the alpha, beta, and gamma substituents on the polymethine bridge.
See this image and copyright information in PMC

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