Synthesis and Spectral Properties of Novel Thionaphtoquinone Dyes

Abstract

2,3-Dichloro-1,4-naphtoquinone 1 compound was reacted with octadecanethiol 2 in two different mole ratio. Compound 3 was obtained from the reaction of 1 and 2 in 1:2 mole/mole ratio. Compounds 7 and 8 were obtained from reaction of 1 and 2 in 1:1 mole/mole ratio and known compound 9 was synthesized as by-product in this reaction. Novel compounds 5a-e were obtained from reaction of 1 and related thiols 4a-e. Known compounds 6c and 6e were synthesized as by-product in this reaction. The structures of the compounds were characterized by elemental analysis, UV-vis, FTIR, 1 H-NMR, 13 C-NMR and Mass spectroscopies.

Derivatives of 1,4‐naphthoquinone as visible‐light‐absorbing one‐component photoinitiators for radical polymerisation

“…1,4‐Naphthoquinone exhibits a high quantum yield of intersystem crossing (Φ isc = 0.74 in acetonitrile), and its triplet state reacts with electron and H‐atom donors . Moreover, the alkylo/arylomercapto‐1,4‐naphthoquinones have an absorption band red shifted in comparison with absorption of the parent naphthoquinone . These features encourage us to design various sulfur‐containing initiators for radical polymerisation.…”

A method for dyeing polyester fibres with quinone derivatives and evaluation of their antioxidant activity

“…Naphthoquinone dyes 4a-j were synthesized from the reaction of 1,4-naphthoquinone (1) with alkyl thiols (2 and 3) following the previously reported procedures [11] and confirmed by melting point determination, elemental analysis and IR spectroscopy in comparison with published data [11,12]. Products were isolated by column chromatography on SiO 2 (Fluka Kieselgel 60, particle size 63-200 μm).…”

“…In this study, 2,3-substituted-1,4-naphthoquinone dyes synthesized from 2,3-dichloro-1,4-naphthoquinone and aliphatic thiols were used for dyeing polyester fibers and screened for their antioxidant capacity using the CUPRAC antioxidant assay. The synthesis and the spectral properties of these compounds were reported in our previous studies [11,12]. In this work, the properties of dyeing polyester fibers and the coloristic properties of the dyed materials were investigated.…”

Synthesis and Biological Evaluation of Novel 5,8-Dibromo-2-N-substituted-1,4-Naphthoquinone Derivatives as Potential Antimicrobial Agents

“…A new series of 2-N-1,4-naphthoquinone derivatives (2a-2g) were synthesized via nucleophilic substitution reaction of 2,5,8tribromonaftalin-1,4-dion (1) and one of the following nucleophiles according to known methods with minor modification [6][7][8]: methylamine, ethtylamine, n-buthylamine, 4aminophenol, phenylethylamine, aniline and benzylamine ( Figure 1 and Table 1). The characterizations of the compounds were performed using 1 H and 13 C NMR spectroscopy, elemental analysis, mass spectrometry and IR spectroscopy.…”

“…Dark red needle crystals, 69%, 120 mg, mp 265-267 °C, R f = 0.09 (1:9 ethyl acetate/hexane), 1 H NMR (400 MHz,CDCl 3 ) δ 7.78 (A part of the AB system, J 6,7 =8. 8…”