Molbank

Open AccessCommunication

Novel Synthesis of N-Acetylcysteine Medicine Using an Effective Method

by

Farzaneh Ziaee

and

Mohammad Ziaee

Molbank 2021, 2021(4), M1288; https://doi.org/10.3390/M1288 - 13 Oct 2021

Abstract

N-acetylcysteine (NAC) is mainly administrated as a mucolytic medication, antioxidant supplement, antidote in paracetamol overdose, and a drug for the prevention of diabetic kidney disease. Its effect has been investigated for the treatment of several diseases such as COVID-19. In this work, [...] Read more.

N-acetylcysteine (NAC) is mainly administrated as a mucolytic medication, antioxidant supplement, antidote in paracetamol overdose, and a drug for the prevention of diabetic kidney disease. Its effect has been investigated for the treatment of several diseases such as COVID-19. In this work, an effective method for high-yield synthesis of N-acetylcysteine is proposed. This drug can be synthesized in a single-batch step instead of using a multi-stage process. The proposed method has shown the potential to be considered as an alternative method for producing NAC. The purification process was carried out using suitable solvents to reach a high level of purity. The characterization of the synthesized drug was undertaken through Elemental analysis, Proton Nuclear Magnetic Resonance (¹H NMR), High Performance Liquid Chromatography (HPLC), Fourier Transform Infrared Spectroscopy (FT-IR), and melting point analyses. Full article

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Open AccessShort Note

3-[N-(4-Methoxybenzyl)amino]benzo[de]anthracen-7-one

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and

Molbank 2021, 2021(4), M1287; https://doi.org/10.3390/M1287 - 11 Oct 2021

Abstract

Herein, we describe the synthesis of 3-[N-(4-methoxybenzyl)amino]benzo[de]anthracen-7-one via a two-step procedure including 3-aminobenzanthrone condensation with anisaldehyde and following reduction of obtained imine to appropriate amine by sodium borohydride. The structure of the synthesized compounds was established by elemental analysis, [...] Read more.

Herein, we describe the synthesis of 3-[N-(4-methoxybenzyl)amino]benzo[de]anthracen-7-one via a two-step procedure including 3-aminobenzanthrone condensation with anisaldehyde and following reduction of obtained imine to appropriate amine by sodium borohydride. The structure of the synthesized compounds was established by elemental analysis, nuclear magnetic resonance spectroscopy, mass spectrometry (EI-MS), and infrared spectroscopy (FT-IR) and confirmed by single-crystal X-ray diffraction. The title compound was analyzed by thermal gravimetric analysis, UV/vis, and fluorescence spectroscopy. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

8-[4-(2-Hydroxypropane-2-yl)Phenyl]-1,3,4,4,5,7-Hexamethyl-4-Boron-3a,4a-Diaza-S-Indacene

by

Anastasiya Zobnina

,

Alexander Moskalensky

and

Aleksey Vorob’ev

Molbank 2021, 2021(4), M1286; https://doi.org/10.3390/M1286 - 08 Oct 2021

Abstract

During recent years, the BODIPY core became a popular scaffold for designing photoremovable protecting groups (PPG). In this paper, we report the synthesis of a new molecule—8-[4-(2-hydroxypropane-2-yl)phenyl]-1,3,4,4,5,7-hexamethyl-4-boron-3a,4a-diaza-S-indacene—by the treatment of meso-(4-CO₂Me-phenyl)-BODIPY with excess of [...] Read more.

During recent years, the BODIPY core became a popular scaffold for designing photoremovable protecting groups (PPG). In this paper, we report the synthesis of a new molecule—8-[4-(2-hydroxypropane-2-yl)phenyl]-1,3,4,4,5,7-hexamethyl-4-boron-3a,4a-diaza-S-indacene—by the treatment of meso-(4-CO₂Me-phenyl)-BODIPY with excess of MeMgI. The product was characterized by ¹H, ¹³C NMR and HRMS. The combination of BODIPY core with tertiary benzilyc alcohol might be promising for utilizing this molecule as visible light removable PPG. Full article

(This article belongs to the Section Organic Synthesis)

Open AccessShort Note

Naphthalen-2-yl 1-(Benzamido(diethoxyphosphoryl)methyl)-1H-1,2,3-triazole-4-carboxylate

by

Serigne Abdou Khadir Fall

,

Sara Hajib

,

Oumaima Karai

,

Salaheddine Boukhssas

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,

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and

Molbank 2021, 2021(4), M1285; https://doi.org/10.3390/M1285 - 04 Oct 2021

Abstract

We have previously published new biheterocyclic phospohonic -amino esters of the 1,2,3-triazole-benzimidazole and 1,2,3-triazole-carbazole type. The aim of the present paper was to describe a new phosponic aminoester bearing a triazole ring substituted in position 5 by an ester group. Thus, according to [...] Read more.

We have previously published new biheterocyclic phospohonic -amino esters of the 1,2,3-triazole-benzimidazole and 1,2,3-triazole-carbazole type. The aim of the present paper was to describe a new phosponic aminoester bearing a triazole ring substituted in position 5 by an ester group. Thus, according to the same catalytic process used previously, the compound naphthalen-2-yl 1-(benzamido(diethoxyphosphoryl)methyl)-1H-1,2,3-triazole-4-carboxylate was synthesized with an excellent yield and high regioselectivity via the copper (I)-catalyzed alkyne–azide cycloaddition reaction (CuAAC), using diethyl (-azido(benzamido)methyl)phosphonate (1) as a dipole and 2- naphthyl propiolate as a dipolarophile (2). The structure of the new compound was fully characterized by 1D (³¹P, ¹H, ¹³C) and 2D (¹H-¹H and ¹H-¹³C) NMR spectroscopy, IR, and HRMS. Full article

(This article belongs to the Special Issue Metal-Catalyzed Synthesis)

Open AccessReview

Synthesis and Characterization of Novel Thiazolidinones and Thioxothiazolidinones Derived from Substituted Indole

by

Nawel Rekiba

,

Abdelmadjid Benmohammed

,

Sofiane Khanoussi

,

Ayada Djafri

and

Jérôme Thibonnet

Molbank 2021, 2021(4), M1284; https://doi.org/10.3390/M1284 - 30 Sep 2021

Abstract

Based on recent discoveries concerning the numerous biological properties of thiazolidinones and thiosemicarbazones, new N-substituted heterocyclic derivatives have been designed by combining the indole ring with thioxothiazolidinone, thiazolidinone or thiosemicarbazone. Thus, a series of new thioxothiazolidinone, thiazolidinone, or thiosemicarbazone derivatives bearing indole-based [...] Read more.

Based on recent discoveries concerning the numerous biological properties of thiazolidinones and thiosemicarbazones, new N-substituted heterocyclic derivatives have been designed by combining the indole ring with thioxothiazolidinone, thiazolidinone or thiosemicarbazone. Thus, a series of new thioxothiazolidinone, thiazolidinone, or thiosemicarbazone derivatives bearing indole-based moiety have been designed, synthesized, and developed in good yields. Full article

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Open AccessShort Note

2,2-Bis(phenylselanyl)-1-(p-tolyl)vinyl 2-Oxo-2-(p-tolyl)acetate

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and

Molbank 2021, 2021(4), M1283; https://doi.org/10.3390/M1283 - 28 Sep 2021

Abstract

2,2-Bis(phenylselanyl)-1-(p-tolyl)vinyl 2-oxo-2-(p-tolyl)acetate was synthesized via the reaction of p-tolylacetylene with diphenyl diselenide and benzoyl peroxide in benzene under atmospheric conditions. The molecular structure of the synthesized compound was evaluated using single-crystal X-ray analysis and spectral analyses. The process [...] Read more.

2,2-Bis(phenylselanyl)-1-(p-tolyl)vinyl 2-oxo-2-(p-tolyl)acetate was synthesized via the reaction of p-tolylacetylene with diphenyl diselenide and benzoyl peroxide in benzene under atmospheric conditions. The molecular structure of the synthesized compound was evaluated using single-crystal X-ray analysis and spectral analyses. The process reported here provides a rare example of the direct and selective transformation of a terminal alkyne to the corresponding geminal diseleno-substituted alkene. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessEditorial

Nitrogen-Containing Molecules: Natural and Synthetic Products including Coordination Compounds

by

Dimitris Matiadis

and

Eleftherios Halevas

Molbank 2021, 2021(4), M1282; https://doi.org/10.3390/M1282 - 27 Sep 2021

Abstract

Nitrogen constitutes one of the most crucial elements in synthetic compounds, both in organic and in coordination chemistry [...] Full article

(This article belongs to the Special Issue Nitrogen-Containing Molecules: Natural and Synthetic Products Including Coordination Compounds)

Open AccessShort Note

5-[4-(tert-Butyl)cyclohexylidene]-2-thioxothiazolidin-4-one

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Molbank 2021, 2021(4), M1281; https://doi.org/10.3390/M1281 - 24 Sep 2021

Abstract

The Knoevenagel reaction is an essential synthetic tool in the organic and medicinal chemistry of thiazolidin-4-one derivatives. In the present work, the application of ethylenediamine diacetate (EDDA) as an effective catalyst for the interaction of 2-thioxothiazolidin-4-one with 4-(tert-butyl)cyclohexanone is proposed. The [...] Read more.

The Knoevenagel reaction is an essential synthetic tool in the organic and medicinal chemistry of thiazolidin-4-one derivatives. In the present work, the application of ethylenediamine diacetate (EDDA) as an effective catalyst for the interaction of 2-thioxothiazolidin-4-one with 4-(tert-butyl)cyclohexanone is proposed. The structure of novel synthesized 5-[4-(tert-butyl)cyclohexylidene]-2-thioxothiazolidin-4-one (yield 61%) was confirmed by ¹H-, ¹³C-NMR, LC-MS, IR, and UV spectra. Drug-like properties of the synthesized compound were evaluated in silico using the SwissAdme, and their potential antimicrobial activity against 15 strains of Gram-positive and Gram-negative bacteria as well as yeasts was evaluated in vitro. The synthesized compound possesses satisfactory drug-like parameters and promising antimicrobial properties and presents interest as a prospective intermediate for the forthcoming design of biologically active small molecules. Full article

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Open AccessCommunication

Hybrid Pyridine Bis-Anthracene-Imidazolium Salt: NMR Studies on Zn-Acetate Complexation

by

Dorina Amăriucăi-Mantu

,

Violeta Mangalagiu

,

Catalina-Ionica Ciobanu

and

Vasilichia Antoci

Molbank 2021, 2021(3), M1280; https://doi.org/10.3390/M1280 - 14 Sep 2021

Abstract

We report here the design and synthesis of a new hybrid bis-anthracene-imidazolium salt, having a pyridine scaffold. NMR studies of dimer generation, as well as complexation with zinc acetate were performed. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

2-Oxo-2H-chromen-7-yl 4-chlorobenzoate

by

Diana Becerra

,

Jaime Portilla

and

Juan-Carlos Castillo

Molbank 2021, 2021(3), M1279; https://doi.org/10.3390/M1279 - 14 Sep 2021

Abstract

We describe the synthesis of 2-oxo-2H-chromen-7-yl 4-chlorobenzoate 3 in 88% yield by the O-acylation reaction of 7-hydroxy-2H-chromen-2-one 1 with 4-chlorobenzoyl chloride 2 in dichloromethane using a slight excess of triethylamine at 20 °C for 1 h. The ester [...] Read more.

We describe the synthesis of 2-oxo-2H-chromen-7-yl 4-chlorobenzoate 3 in 88% yield by the O-acylation reaction of 7-hydroxy-2H-chromen-2-one 1 with 4-chlorobenzoyl chloride 2 in dichloromethane using a slight excess of triethylamine at 20 °C for 1 h. The ester 3 was completely characterized by mass spectrometry, IR, UV–Vis, 1D, and 2D NMR spectroscopy. Full article

(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)

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Open AccessShort Note

4,6-Bis((E)-2-(4′-N,N-diphenylamino-[1,1′-biphenyl]-4-yl)vinyl)-2-phenylpyrimidine

by

Lacina Diarra

,

Françoise Robin-le Guen

and

Sylvain Achelle

Molbank 2021, 2021(3), M1278; https://doi.org/10.3390/M1278 - 10 Sep 2021

Abstract

In this contribution, we designed a 4,6-distyrylpyrimidine chromophore with diphenylamino electron-donating groups and biphenylenevinylene extended π-conjugated linkers. This compound has been synthesized in two steps from 4,6-dimethyl-2-phenylpyrimidine by a double Knoevenagel reaction with 4-bromobenzaldehyde followed by a double Suzuki–Miyaura cross coupling reaction with [...] Read more.

In this contribution, we designed a 4,6-distyrylpyrimidine chromophore with diphenylamino electron-donating groups and biphenylenevinylene extended π-conjugated linkers. This compound has been synthesized in two steps from 4,6-dimethyl-2-phenylpyrimidine by a double Knoevenagel reaction with 4-bromobenzaldehyde followed by a double Suzuki–Miyaura cross coupling reaction with 4-(N,N-diphenylamino)phenylboronic acid. This compound exhibits intense emission in moderately polar solvents as well as in solid state. This compound is characterized by an intense emission solvatochromism with emission ranging from blue in non polar n-heptane to orange in dichloromethane. This chromophore is also sensible to the presence of acid with a bathochromic shift of the charge transfer absorption band and emission quenching. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessArticle

2-Chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]styryl}pyrimidine: Synthesis, Spectroscopic and Computational Evaluation

by

Otávio Augusto Chaves

,

Vitor Sueth-Santiago

,

Douglas Chaves de Alcântara Pinto

,

José Carlos Netto-Ferreira

,

Debora Decote-Ricardo

and

Marco Edilson Freire de Lima

Molbank 2021, 2021(3), M1276; https://doi.org/10.3390/M1276 - 07 Sep 2021

Abstract

A novel curcumin analog namely 2-chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]-styryl}pyrimidine (compound 7) was synthesized by three-step reaction. The condensation reaction of protected vanillin with 2-chloro-4,6-dimethylpyrimidine (6) was the most efficient step, resulting in a total yield of 72%. The characterization [...] Read more.

A novel curcumin analog namely 2-chloro-4,6-bis{(E)-3-methoxy-4-[(4-methoxybenzyl)oxy]-styryl}pyrimidine (compound 7) was synthesized by three-step reaction. The condensation reaction of protected vanillin with 2-chloro-4,6-dimethylpyrimidine (6) was the most efficient step, resulting in a total yield of 72%. The characterization of compound 7 was performed by ¹H and ¹³C nuclear magnetic resonance (NMR), as well as high-resolution mass spectrometry. The experimental spectrometric data were compared with the theoretical spectra obtained by the density functional theory (DFT) method, showing a perfect match between them. UV-visible spectroscopy and steady-state fluorescence emission studies were performed for compound 7 in solvents of different polarities and the results were correlated with DFT calculations. Compound 7 showed a solvatochromism effect presenting higher molar extinction coefficient (log ε = 4.57) and fluorescence quantum yield (ϕ = 0.38) in toluene than in acetonitrile or methanol. The simulation of both frontier molecular orbitals (FMOs) and molecular electrostatic potential (MEP) suggested that the experimental spectra profile in toluene was not interfered by a possible charge transfer. These results are an indication of a low probability of compound 7 in reacting with unsaturated phospholipids in future applications as a fluorescent dye in biological systems. Full article

(This article belongs to the Special Issue Synthesis of Flavonoids or Other Nature-Inspired Small Molecules)

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Graphical abstract

Open AccessShort Note

2,6-Dimethoxybenzyl Bromide

by

R. Alan Aitken

,

Elizabeth A. Saab

and

Alexandra M. Z. Slawin

Molbank 2021, 2021(3), M1277; https://doi.org/10.3390/M1277 - 07 Sep 2021

Abstract

The unstable title compound has been characterized for the first time. Its melting point, UV, IR, ¹H and ¹³C-NMR and high-resolution mass spectra are presented. The X-ray structure has also been determined and shows a rather long C–Br bond perpendicular to [...] Read more.

The unstable title compound has been characterized for the first time. Its melting point, UV, IR, ¹H and ¹³C-NMR and high-resolution mass spectra are presented. The X-ray structure has also been determined and shows a rather long C–Br bond perpendicular to the otherwise planar molecule. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Open AccessCommunication

Practical and Asymmetric Synthesis of Apremilast Using Ellman’s Sulfinamide as a Chiral Auxiliary

by

Bofei Wang

and

Fangrui Zhong

Molbank 2021, 2021(3), M1275; https://doi.org/10.3390/M1275 - 02 Sep 2021

Abstract

Herein, we described a new protocol for the asymmetric synthesis of apremilast using tert-butanesulfinamide as a chiral auxiliary. This synthetic route consisted of four steps starting from the commercially available 3-hydroxy-4-methoxybenzaldehyde, and apremilast was accordingly obtained in an overall 56% yield and [...] Read more.

Herein, we described a new protocol for the asymmetric synthesis of apremilast using tert-butanesulfinamide as a chiral auxiliary. This synthetic route consisted of four steps starting from the commercially available 3-hydroxy-4-methoxybenzaldehyde, and apremilast was accordingly obtained in an overall 56% yield and with 95.5% ee. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessCommunication

4-(((4-Methoxyphenyl)amino)methyl)-N,N-dimethylaniline and 2-Methoxy-5-((phenylamino)methyl)phenol

by

Peter A. Ajibade

and

Fartisincha P. Andrew

Molbank 2021, 2021(3), M1274; https://doi.org/10.3390/M1274 - 31 Aug 2021

Abstract

Molecular structures of 4-(((4-methoxyphenyl)amino)methyl)-N,N-dimethylaniline and 2-methoxy-5-((phenylamino)methyl)phenol synthesized via Schiff bases reduction route are reported. The compounds consist of asymmetric units of C₁₆H₂₀N₂O (1) and C₁₄H₁₅NO₂ ( [...] Read more.

Molecular structures of 4-(((4-methoxyphenyl)amino)methyl)-N,N-dimethylaniline and 2-methoxy-5-((phenylamino)methyl)phenol synthesized via Schiff bases reduction route are reported. The compounds consist of asymmetric units of C₁₆H₂₀N₂O (1) and C₁₄H₁₅NO₂ (2) in orthorhombic and monoclinic crystal systems, respectively. Compound 1 consist of intermolecular C11—H11···N2 hydrogen bonding with C11···N21 = 3.463(4) Å. The hydroxyl group in 2 is also involved in intermolecular O2—H2···O2 and O2—H2···O21 hydrogen bonding with O2···O11 = 2.8885(15) Å and O1···O21 = 2.9277(5) Å. The molecular structures of the compounds are stabilized by secondary intermolecular interactions of C1—H1B···O11 and C5—H···(C41, C51, C61, C71) for 1 and H···C, C—H···O and N—H···C for 2. The reported compounds are important starting material for the synthesis of many compounds such as azo dyes and dithiocarbamate. Full article

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Open AccessCommunication

Synthesis of 4-[(1H-Benzimidazol-2-yl)sulfanyl]benzaldehyde and 2-({4-[(1H-Benzimidazol-2-yl)sulfanyl]phenyl}methylidene)hydrazine-1-carbothioamide

by

Mustafa Turki Ubeid

,

Hamdy Khamees Thabet

and

Mohamed Yousef Abu Shuheil

Molbank 2021, 2021(3), M1273; https://doi.org/10.3390/M1273 - 26 Aug 2021

Cited by 1

Abstract

Here we describe the preparation of 2-(4-((1H-benzo[d]imidazol-2-yl)thio)-benzylidene)-hydrazine-1-carbothioamide in two steps. In the first step, 1,3-dihydro-2H-1,3-benzimidazole-2-thione was reacted with 4-fluorobenzaldehyde in DMSO to get 4-[(1H-benzimidazol-2-yl)sulfanyl]benzaldehyde in high yield. The reaction of the obtained aldehyde with thiosemicarbazide in ethanol at reflux [...] Read more.

Here we describe the preparation of 2-(4-((1H-benzo[d]imidazol-2-yl)thio)-benzylidene)-hydrazine-1-carbothioamide in two steps. In the first step, 1,3-dihydro-2H-1,3-benzimidazole-2-thione was reacted with 4-fluorobenzaldehyde in DMSO to get 4-[(1H-benzimidazol-2-yl)sulfanyl]benzaldehyde in high yield. The reaction of the obtained aldehyde with thiosemicarbazide in ethanol at reflux temperature yielded 2-({4-[(1H-benzimidazol-2-yl)sulfanyl]phenyl}methylidene)hydrazine-1-carbothioamide. The structure of the synthesized compounds was established by NMR spectroscopy (¹H, ¹³C), mass spectrometry, and infrared spectroscopy. Full article

(This article belongs to the Special Issue Nitrogen-Containing Molecules: Natural and Synthetic Products Including Coordination Compounds)

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Open AccessShort Note

3-(3-Hydroxypropyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxaldehyde Methyl Hemiacetal

by

Massimiliano Cordaro

Molbank 2021, 2021(3), M1272; https://doi.org/10.3390/M1272 - 20 Aug 2021

Abstract

The synthesis of 3-(3-hydroxypropyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxaldehyde as a stable methyl hemiacetal through a convenient 3-step procedure is reported. The molecule is multifunctional as it contains a formyl group, a hydroxyl group and the imide moiety. Each of these groups can play a role in specific [...] Read more.

The synthesis of 3-(3-hydroxypropyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxaldehyde as a stable methyl hemiacetal through a convenient 3-step procedure is reported. The molecule is multifunctional as it contains a formyl group, a hydroxyl group and the imide moiety. Each of these groups can play a role in specific transformations or uses. Full article

(This article belongs to the Section Organic Synthesis)

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Graphical abstract

Open AccessShort Note

5-(2,6-Diacetamidopyridin-4-yl)-kryptoBODIPY

by

Massimiliano Cordaro

and

Mariachiara Trapani

Molbank 2021, 2021(3), M1271; https://doi.org/10.3390/M1271 - 13 Aug 2021

Abstract

The development of new dyes for various fields of application is of primary interest for the scientific community, among these BODIPY are widely studied for their versatility. This communication describes the synthesis of a BODIPY dye on which a diacetoamidopyridine moiety is connected [...] Read more.

The development of new dyes for various fields of application is of primary interest for the scientific community, among these BODIPY are widely studied for their versatility. This communication describes the synthesis of a BODIPY dye on which a diacetoamidopyridine moiety is connected in meso position. The synthesis procedure requires a one-pot step and the dye is obtained with a yield of 20%. The diacetoamido portion contains chemical functionalities able to favor the interaction of BODIPY with complementary molecules, such as uracil or thymine, offering potential applications for the design of new functional materials or sensors. Full article

(This article belongs to the Section Organic Synthesis)

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Open AccessShort Note

2-((E)-2-((E)-4-Chloro-5-(2-((E)-5-methoxy-3,3-dimethyl-1-(3-phenylpropyl)indolin-2-ylidene) ethylidene)-1,1-dimethyl-1,2,5,6-tetrahydropyridin-1-ium-3-yl)vinyl)-5-methoxy-3,3-dimethyl-1-(3-phenylpropyl)-3H-indol-1-ium

by

Emmanuel Ramsey Buabeng

and

Maged Henary

Molbank 2021, 2021(3), M1270; https://doi.org/10.3390/M1270 - 11 Aug 2021

Abstract

A heptamethine fluorophore, ERB-60, has been synthesized efficiently in four steps in a good yield. The structure of this fluorophore consists of an electron-donating group (methoxy), a hydrophobic moiety (phenylpropyl) with a rotatable bond, a quaternary ammonium fragment, and indolium rings at [...] Read more.

A heptamethine fluorophore, ERB-60, has been synthesized efficiently in four steps in a good yield. The structure of this fluorophore consists of an electron-donating group (methoxy), a hydrophobic moiety (phenylpropyl) with a rotatable bond, a quaternary ammonium fragment, and indolium rings at the terminal ends connected via polymethine chain. All these inherent chemical features fine-tuned the optical properties of the fluorophore. This compound was characterized by both ¹H NMR, ¹³C NMR and mass spectra. The optical properties, including molar absorptivity, fluorescence, Stokes’s shift, and quantum yield, were measured in different solvents such as DMSO, DMF, MeCN, i-PrOH, MeOH, and H₂O. The wavelengths of maximum absorbance of ERB-60 were found to be in the range of 745–770 nm based on the solvents used. In decreasing order, the maximum wavelength of absorbance of ERB-60 in the tested solvents was DMSO > DMF > i-PrOH > MeOH > MeCN > H₂O while the decreasing order of the extinction coefficient was found to be MeCN > MeOH > DMSO > i-PrOH > H₂O > DMF. ERB-60 was found to be more photostable than IR-786 iodide, a commercially available dye, and brighter than the FDA-approved dye, indocyanine green (ICG). Full article

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