An infrared squaraine dye was utilized to detect Cu2+ in solvents based on H-aggregates of squaraine dye. H-aggregates are a type of aggregation with enhanced photophysical properties compared to monomers. In the presence of a Ca2+ solution, F–Cl offers exceptional H-aggregators that can be transformed into monomers by adding Cu2+. Furthermore, this mode successfully demonstrated fluorescence changes in HeLa cells cultured in vitro after the addition of Ca2+ or Cu2+. A highly specific detection of Cu2+ was achieved using this transformation mode.
QiuY.YuanB.CaoY.HeX., et al. “Recent Progress on Near-Infrared Fluorescence Heptamethine Cyanine Dye-Based Molecules and Nanoparticles for Tumor Imaging and Treatment”. Wiley Interdiscip. Rev.: Nanomed. Nanobiotechnol. 2023. 15(5): e1910. https://doi.org/10.1002/wnan.1910
2.
BiliciK.CetinS.CelikbasE.Yagci AcarH., et al. “Recent Advances in Cyanine-Based Phototherapy Agents”. Front. Chem. 2021. 9: 07876. https://doi.org/10.3389/fchem.2021.707876
3.
MaX.ShiL.ZhangB.LiuL., et al. “Recent Advances in Bioprobes and Biolabels Based on Cyanine Dyes”. Anal. Bioanal. Chem. 2022. 414(16): 4551–4573. https://doi.org/10.1007/s00216-022-03995-8
4.
CaoW.SlettenE.M.. “Fluorescent Cyanine Dye J-Aggregates in the Fluorous Phase”. J. Am. Chem. Soc. 2018. 140(8): 2727–2730. https://doi.org/10.1021/jacs.7b11925
5.
DarN.AnkariR.. “Theoretical Models, Preparation, Characterization and Applications of Cyanine J-Aggregates: A Minireview”. ChemistryOpen. 2022. 11(11): e202200103. https://doi.org/10.1002/open.202200103
6.
KumarV.BakerG.PandeyS.. “Ionic Liquid-Controlled J- Versus H-Aggregation of Cyanine Dyes”. Chem. Commun. 2011. 47(16): 4730–4732. https://doi.org/10.1039/c1cc00080b
7.
GuanA.J.ZhangJ.WangL.CuiJ., et al. “Spontaneous Formation and Reversible Transformation Between Achiral J- and Chiral H-Aggregates of Cyanine Dye MTC”. RSC Adv. 2019. 9(20): 11365–11368. https://doi.org/10.1039/c9ra00063a
8.
YuL.ZhangY.DingC.ShiX.. “Disassembly of Dimeric Cyanine Dye Supramolecular Assembly by Tetramolecular G-Quadruplex Dependence on Linker Length and Layers of G-Quartet”. Molecules. 2019. 24(10): 2015. https://doi.org/10.3390/molecules24102015
9.
NicoliF.RoosM.K.HemmigE.A.AntonioM.D., et al. “Proximity-Induced H-Aggregation of Cyanine Dyes on DNA-Duplexes”. J. Phys. Chem. A. 2016. 120(50): 9941–9947. https://doi.org/10.1021/acs.jpca.6b10939
10.
ZhuS.TianR.AntarisA.L.ChenX.DaiH.. “Near-Infrared-II Molecular Dyes for Cancer Imaging and Surgery”. Adv. Mater. 2019. 31(24): e1900321. https://doi.org/10.1002/adma.201900321
11.
QianH.ChengQ.TianY.DangH., et al. “An Anti-Aggregation NIR-II Heptamethine-Cyanine Dye with a Stereo-Specific Cyanine for Imaging-Guided Photothermal Therapy”. J. Mater. Chem. B. 2021. 9(11): 2688–2696. https://doi.org/10.1039/d1tb00018g
12.
JinT.ChengD.JiangG.XingW., et al. “Engineering Naphthalimide-Cyanine Integrated Near-Infrared Dye Into ROS-Responsive Nanohybrids for Tumor PDT/PTT/Chemotherapy”. Bioact. Mater. 2021. 14: 42–51. https://doi.org/10.1016/j.bioactmat.2021.12.009
HeC.ZhouH.YangN.NiuN., et al. “A Turn-On Fluorescent BOPHY Probe for Cu2+ Ion Detection”. New J. Chem. 2018. 42(4): 2520–2525. https://doi.org/10.1039/C7NJ03911E
15.
GaoJ.YinJ.TaoZ.LiuY., et al. “An Ultrasensitive Fluorescence Sensor with Simple Operation for Cu2+ Specific Detection in Drinking Water”. ACS Omega. 2018. 3(3): 3045–3050. https://doi.org/10.1021/acsomega.7b01497
16.
LiH.TangY.ShenK.LuJ., et al. “NIR Squaraine Dyes for Dual Colorimetric and Fluorescent Determination of Fe3+, Cu2+, and Hg2+ Ions”. RSC Adv. 2023. 13(25): 17202–17211. https://doi.org/10.1039/d3ra02419a
17.
WangW.FuA.YouJ.GaoG., et al. “Squaraine-Based Colorimetric and Fluorescent Sensors for Cu2+-Specific Detection and Fluorescence Imaging in Living Cells”. Tetrahedron. 2010. 66(21): 3695–3701. https://doi.org/10.1016/j.tet.2010.03.070
18.
YuL.FanX.ZhaoH.DingC., et al. “A Near-Infrared Squaraine Dye for Cu2+-Specific Detection and Fluorescence Imaging in Living Cells and Mice”. Dyes Pigm. 2022. 206: 110600. https://doi.org/10.1016/j.dyepig.2022.110600
19.
ZhouH.-J.RenT.-B.. “Recent Progress of Cyanine Fluorophores for NIR-II Sensing and Imaging”. Chem. Asian J. 2022. 17(8): e202200147. https://doi.org/10.1002/asia.202200147
20.
SunW.GuoS.HuC.FanJ., et al. “Recent Development of Chemosensors Based on Cyanine Platforms”. Chem. Rev. 2016. 116(14): 7768–7817. https://doi.org/10.1021/acs.chemrev.6b00001
21.
SlavnovaT.D.ChibisovA.K.GörnerH.. “Kinetics of Salt-Induced J-Aggregation of Cyanine Dyes”. J. Phys. Chem. A. 2005. 109(21): 4758–4765. https://doi.org/10.1021/jp058014k
22.
ArmitageB.RettererJ.O'BrienD.. “Dimerization of Cyanine Dyes in Water Driven by Association with Hydrophobic Borate Anions”. J. Am. Chem. Soc. 1993. 115(20): 10786–10790. https://doi.org/10.1021/ja00076a040
23.
RengeI.WildU.P.. “Solvent, Temperature, and Excitonic Effects in the Optical Spectra of Pseudoisocyanine Monomer and J-Aggregates”. J. Phys. Chem. A. 1997. 101(43): 7977–7988. https://doi.org/10.1021/jp971371d
DickinsonH.O.. “The Aggregation of Cyanine Dyes in Aqueous Solution”. Trans. Faraday Soc. 1947. 43: 486–491. https://doi.org/10.1039/TF9474300486
26.
SeifertJ.L.ConnorR.E.KushonS.WangM., et al. “Spontaneous Assembly of Helical Cyanine Dye Aggregates on DNA Nanotemplates”. J. Am. Chem. Soc. 1999. 121(13): 2987–2995. https://doi.org/10.1021/ja984279j
27.
BertocchiF.DelledonneA.Vargas-NadalG.TerenzianiF., et al. “Aggregates of Cyanine Dyes: When Molecular Vibrations and Electrostatic Screening Make the Difference”. J. Phys. Chem. C. 2023. 127(21): 10185–10196. https://doi.org/10.1021/acs.jpcc.3c01253
28.
NekrasovA.D.ShapiroB.I.. “Effect of Doubly Charged Metal Cations on J-Aggregation of an Anionic Heptamethine Indocyanine Dye”. High Energy Chem. 2018. 52: 456–462. https://doi.org/10.1134/S0018143918060103
29.
AltmanR.B.ZhengQ.ZhouZ.TerryD.S., et al. “Enhanced Photostability of Cyanine Fluorophores Across the Visible Spectrum”. Nat. Methods. 2012. 9(5): 428–429. https://doi.org/10.1038/nmeth.1988
30.
WeiK.WuY.LiP.ZhengX., et al. “Modulating Planarity of Cyanine Dye to Construct Highly Stable H-Aggregates for Enhanced Photothermal Therapy”. Nano Res. 2023. 16: 970–979. https://doi.org/10.1007/s12274-022-4818-0
31.
MooiS.M.KellerS.N.HeyneB.. “Forcing Aggregation of Cyanine Dyes with Salts: A Fine Line Between Dimers and Higher Ordered Aggregates”. Langmuir. 2014. 30(32): 9654–9662. https://doi.org/10.1021/la502124b
32.
LiZ.MukhopadhyayS.JangS.BrédasJ.JenA.K.-Y.. “Supramolecular Assembly of Complementary Cyanine Salt J-Aggregates”. J. Am. Chem. Soc. 2015. 137(37): 11920–11923. https://doi.org/10.1021/jacs.5b08072
MuthurajB.G.DeshmukhR.TrivediV.IyerP.K.. “Highly Selective Probe Detects Cu2+ and Endogenous NO Gas in Living Cell”. ACS Appl. Mater. Interfaces. 2014. 6(9): 6562–6569. https://doi.org/10.1021/am501476w
35.
BhuniaS.DuttaB.PalK.ChandraA., et al. “Ultra-Trace Level Detection of Cu2+ in an Aqueous Medium by Novel Zn(II)-Dicarboxylato-Pyridyl Coordination Polymers and Cell Imaging with HepG2 Cells”. New J. Chem. 2021. 45(31): 13941–13948. https://doi.org/10.1039/D1NJ00917F
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