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1

Synthesis and Characterization of Isocyanonaphthalene Derivatives

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Acetone, dichloromethane (DCM), n-hexane, 2-propanol, toluene (reagent grade) were obtained from Molar Chemicals, Hungary, and they were purified by atmospheric pressure distillation. Furthermore, acetonitrile (MeCN), tetrahydrofuran (THF), methanol (MeOH), dimethyl-formamide (DMF), dimethyl-sulfoxide (DMSO), pyridine (HPLC grade, VWR, Darmstadt, Germany), ethylacetate (EtOAc), (reagent grade, Molar Chemicals, Hungary), 1,4-dioxane (reagent grade, Reanal, Hungary), 1,4-diaminonaphthalene (Sigma-Aldrich, Schnelldorf, Germany) were used without further purification. 2,6-diaminonaphthalene was purchased from Manchester Organics (London, UK) and purified by column chromatography.
The 1-amino-4-isocyanonaphthalene (1,4-ICAN) and the 2-amino-6-isocyanonaphthalene (2,6-ICAN) isomers were synthesized from the corresponding diamines (1,4- and 2,6-diaminonaphthalene), and the obtained products were characterized similarly to that reported for the 1-amino-5-isocyanonaphthalene [15 (link)]. The details of the synthesis and the characterization of 1,4-ICAN and 2,6-ICAN are given in the Supporting Information.
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Purification and Utilization of Organic Solvents

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Acetone, dichloromethane (DCM), hexane, 2-propanol (iPrOH), toluene, ethyl-acetate (EtOAc) (reagent grade, Molar Chemicals, Hungary) were purified by distillation. Acetonitrile (MeCN), tetrahydrofuran (THF), methanol (MeOH), dimethyl formamide (DMF), dimethyl sulfoxide (DMSO), pyridine (HPLC grade, VWR, Germany), cyclohexane, 1,4-dioxane (reagent grade, Reanal, Hungary), chloroform, 3,6-diaminoacridine hydrochloride (Sigma-Aldrich, Germany), sodium lauryl sulfate (SLS) (Biosolve, France) were used without further purification.
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Purification and Characterization of Organic Solvents

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Acetone, dichloromethane (DCM), hexane, 2-propanol (iPrOH), toluene, ethyl-acetate (EtOAc) (reagent grade, Molar Chemicals, Hungary) were purified by distillation. Acetonitrile (MeCN), tetrahydrofuran (THF), methanol (MeOH), dimethyl formamide (DMF), dimethyl sulfoxide (DMSO), pyridine (HPLC grade, VWR, Germany), cyclohexane, 1,4-dioxane (reagent grade, Reanal, Hungary), chloroform, 1,5-diaminoanthraquinone (Sigma-Aldrich, Germany) were used without further purification.
NMR: 1H and 13C-NMR spectra were recorded in CDCl3 and DMSO-d6 at 25 °C on a Bruker Avance DRX-400 and a Bruker AM 360 spectrometer at 400 and 360 MHz, respectively, with tetramethylsilane as the internal standard.
UV–vis: The UV–vis spectra were recorded on an Agilent Cary 60 spectrophotometer (Agilent, Santa Clara, CA, USA) in a quartz cuvette of 1.00 cm optical length. A 3.00 cm3 solution was prepared from the sample.
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