Dyes and Pigments, volume 198, pages 110011
Synthesis and photophysical properties of metal complexes of curcumin dyes: Solvatochromism, acidochromism, and photoactivity
Publication type: Journal Article
Publication date: 2022-02-01
Journal:
Dyes and Pigments
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 4.5
ISSN: 01437208, 18733743
General Chemical Engineering
Process Chemistry and Technology
Abstract
Curcumin and its dyes have attracted attention due to their environment-sensitivity and optical properties. However, the free molecule has low photoactivity, which is a limitation for use in photodynamic therapy. To overcome this limitation, we proposed the chelation of a D-π-A-π-D curcumin dye (1) with the metals Cu (II) and Pd (II). The photophysical properties of the curcumin dyes were investigated in different solvents, using UV–vis spectroscopy and time-resolved/steady-state fluorescence techniques. In our results, all curcumin dyes exhibited a positive solvatochromism from non-polar to polar solvents, with the Stokes’ shift in the range of 1895–4970 cm−1. The acidochromism studies were performed in chloroform solution and TLC plates using trifluoroacetic acid (TFA). The results exhibited a negative acidochromism and fluorescence quenching upon gradual addition of TFA, demonstrating reversibility upon addition of triethylamine (TEA). The main mechanism which influences the solvatochromism/acidochromism is the ICT system and fluorescence lifetime decays exhibited mono-exponential fit for aprotic solvents and bi-exponential fit for protic solvents (EtOH and MeOH). Compared to the curcumin ligand (1), the metal complexes (1a-b) exhibited higher singlet oxygen quantum yields (ΦΔ = 0.36 and 0.54, respectively). The in vitro antimicrobial photoactivity of the compounds was evaluated against six different microorganisms. The results showed that the metal complexes (1a-b) exhibited both antileishmanial (MIC = 2.29 μM against Leishmania amazonensis promastigotes) and antifungal (IC50 = 10 μM against Sporothrix brasiliensis yeasts) activities, while the ligand showed no activity, suggesting the chelation with the metals Cu (II) and Pd (II) may improve its photoactivity.
Top-30
Citations by journals
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1 publication, 6.25%
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Russian Chemical Reviews
1 publication, 6.25%
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1 publication, 6.25%
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1 publication, 6.25%
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1 publication, 6.25%
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1 publication, 6.25%
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1 publication, 6.25%
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Citations by publishers
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Elsevier
5 publications, 31.25%
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3 publications, 18.75%
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Wiley
3 publications, 18.75%
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American Chemical Society (ACS)
2 publications, 12.5%
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Springer Nature
1 publication, 6.25%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 6.25%
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Royal Society of Chemistry (RSC)
1 publication, 6.25%
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- We do not take into account publications without a DOI.
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- Statistics recalculated weekly.
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de França B.M. et al. Synthesis and photophysical properties of metal complexes of curcumin dyes: Solvatochromism, acidochromism, and photoactivity // Dyes and Pigments. 2022. Vol. 198. p. 110011.
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de França B.M., Oliveira S.S., Souza L.O., Mello T.P., Santos A.L., Bello Forero J.S. Synthesis and photophysical properties of metal complexes of curcumin dyes: Solvatochromism, acidochromism, and photoactivity // Dyes and Pigments. 2022. Vol. 198. p. 110011.
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TY - JOUR
DO - 10.1016/j.dyepig.2021.110011
UR - https://doi.org/10.1016/j.dyepig.2021.110011
TI - Synthesis and photophysical properties of metal complexes of curcumin dyes: Solvatochromism, acidochromism, and photoactivity
T2 - Dyes and Pigments
AU - de, França
AU - Oliveira, S S
AU - Souza, L O
AU - Mello, T P
AU - Santos, A L
AU - Bello, Forero
PY - 2022
DA - 2022/02/01 00:00:00
PB - Elsevier
SP - 110011
VL - 198
SN - 0143-7208
SN - 1873-3743
ER -
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@article{2022,
author = {França de and S S Oliveira and L O Souza and T P Mello and A L Santos and Forero Bello},
title = {Synthesis and photophysical properties of metal complexes of curcumin dyes: Solvatochromism, acidochromism, and photoactivity},
journal = {Dyes and Pigments},
year = {2022},
volume = {198},
publisher = {Elsevier},
month = {feb},
url = {https://doi.org/10.1016/j.dyepig.2021.110011},
pages = {110011},
doi = {10.1016/j.dyepig.2021.110011}
}