Stability in solution of indolium heptamethine cyanines and related pH‐sensitive systems

Strękowski, Lucjan; Mason, Joan; Say, Martial; Patonay, Gábor

doi:10.1002/jhet.5570440233

Cited by 14 publications

(6 citation statements)

References 22 publications

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“…2-((E)-2-((E)-2-chloro-3-(2-((E)-1,3,3-trimethylindolin-2-ylidene)ethylidene)cyclohex-1-en-1-yl)vinyl)-1,3,3-trimethyl-3H-indol-1-ium iodide, 4a : was synthesized as previously described. Stability in solution of indolium heptamethine cyanines and related pH-sensitive systems 26 1 H NMR (400 MHz, DMSO- d 6 ) δ 1.67 (s, 12 H), 1.85 (m, 2 H), 2.72 (t, J = 6.0 Hz, 4 H), 3.68 (s, 6 H), 6.30 (t, J = 14.4 Hz, 2 H), 7.28 (m, 2 H), 7.44 (m, 4 H), 7.62 (d, J = 7.2 Hz, 2 H), 8.25 (d, J = 14.4 Hz, 2 H).…”

Section: Methodsmentioning

confidence: 99%

Introduction of various substitutions to the methine bridge of heptamethine cyanine dyes Via substituted dianil linkers

Levitz

Marmarchi

Henary

2018

Photochem Photobiol Sci

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The unique optical properties of cyanine dyes have prompted their use in numerous applications. Heptamethine cyanines are commonly modified on the methine bridge after synthesis of a meso-chlorine containing cyanine. Herein, a series of heptamethine cyanines containing modified methine bridges were synthesized using substituted dianil linkers. Their optical properties including, molar absorptivity, fluorescence, and quantum yield were measured as well as their hydrophobic effects in polar buffer solution. It was shown that dyes containing cyclopentene in the methine bridge or a phenyl ring in the meso position display increased molar absorptivity while the increased flexibility of the dye containing a cycloheptene in the methine bridge prevented fluorescence.

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Section: Methodsmentioning

confidence: 99%

Introduction of various substitutions to the methine bridge of heptamethine cyanine dyes Via substituted dianil linkers

Levitz

Marmarchi

Henary

2018

Photochem Photobiol Sci

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“…The nitrogens in the cyanine chain still exhibit low nucleophilicity since electron density distributes over the entire methine chain. Thus, protonation of the nitrogen in the cyanine moiety occurs with less efficiency compared to amines [117]. This strategy helped to enable cationic photopolymerization with cyanine as sensitizers combined with 88 as PF 6 − -salt.…”

Section: Polymer Synthesis Nir Sensitized Radical Photopolymerizationmentioning

confidence: 99%

Photophysics and photochemistry of NIR absorbers derived from cyanines: key to new technologies based on chemistry 4.0

Strehmel¹,

Schmitz²,

Kütahya³

et al. 2020

Beilstein J. Org. Chem.

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Cyanines derived from heptamethines were mainly discussed regarding their functionalization to broaden the solubility in different surroundings exhibiting either hydrophilic or hydrophobic properties and to tailor made the ΔG et photopysical properties with respect to absorption and fluorescence. Electrochemical properties were additionally considered for some selected examples. The cyanines chosen comprised as end groups either indolenine, benzo[e]- or benzo[cd]indolium pattern, which facilitated to shift the absorption between 750–1000 nm. This enabled their use in applications with light sources emitting in the near-infrared (NIR) region selected from high power LEDs or lasers with line-shaped focus. The absorbers considered were discussed regarding their function as sensitizer for applications related to Chemistry 4.0 standards. These were mainly photopolymer coatings, which can be found for applications in the graphic industry or to protect selected substrates. The huge release of heat on demand upon turning ON or OFF the NIR light source enables them for photothermal treatment in processes requesting heat to initiate either chemical (activated reactions) or physical (melting, evaporation) events.

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“…N-alkylbenzo [c,d]indolium salts were used as starting compounds to prepare the squaraine dyes. The synthetic route to the starting compounds 10 and 11 involved five steps starting with 1 (Scheme 1) as described in literature (Strekowski et al, 2007).…”

Section: Discussionmentioning

confidence: 99%

Synthesis of symetrical near-infrared dyes containing benzo[c,d]indole system

Say¹,

Timothée²,

Akpa³

et al. 2019

Int. J. Bio. Chem. Sci

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Five symmetrical near infrared dyes having different linker between the two heterocycles were synthesized by condensation of N-alkylbenzo[c,d]indolium salts with either squaric acid or imine. All synthesized dyes showed strong absorbance in the near-infrared region of 850-1015 nm and can be used as nucleic acid detection or fluorescent labeling agents for proteins. Three of the dyes 21, 22 and 25 containing functionalized N-substituents (ester group) can be further modified or covalently attached to target. The structures of these cyanine dyes where characterized by virtue of NMR, UV, MALDI and Elemental analysis.

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Stability in solution of indolium heptamethine cyanines and related pH‐sensitive systems

Abstract: Relative stabilities of methanolic solutions of dyes that are potentially important for labeling of biological macromolecules with a visible‐red or near‐infrared fluorophore were evaluated in the presence of molecular oxygen under dark and light conditions.

Cited by 14 publications

References 22 publications

Introduction of various substitutions to the methine bridge of heptamethine cyanine dyes Via substituted dianil linkers

Introduction of various substitutions to the methine bridge of heptamethine cyanine dyes Via substituted dianil linkers

Photophysics and photochemistry of NIR absorbers derived from cyanines: key to new technologies based on chemistry 4.0

Synthesis of symetrical near-infrared dyes containing benzo[c,d]indole system

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