Study Of Indole Derivatives And Their Complexes

As marine environmental protection is highly prized, the research ofenvironmentally friendly antifoulants is of great significance. Two new kinds ofantifoulants with high efficiency and low toxicity have been studied in this paper:indole derivatives and metal complexes. A series of N-substituted indole derivativeshave been synthetized by Michael reaction, which are further adopted as raw materialsto obtain target compounds by Mannich reaction and Friedel-Crafts reaction,respectively.4new indole derivatives have been finally synthetized, which can bedivided into two categories: gramine compounds and acrylamide compoundscontaining indole structures. Two single-crystal complexes have been obtained bydirect reaction method and diffusion method. They are listed as follows:1. Indole derivativesN-（（1-propanoate-1H-indole-3-yl）methyl）acrylamide（IMP-N）N-（（5-bromo-1-propanoate-1H-indole-3-yl）methyl）acrylamide（BrIMP-N）N-（（5,6-dichloro-1-propanoate-1H-indole-3-yl） ethyl）acrylamide（BrIEP-N）3-（3-（（dimethylamino）methyl）-5-bromo-1H-indole-1-yl）-N-allypropanamide（BrG-A-PD）All of the indole derivatives were characterized by IR spectroscopy and NMR.The optimum reaction conditions of IMP-N、BrIMP-N、BrIEP-N were studied. Thesynthetic route of BrG-A-PD was improved, which increased their yields and reducedthe difficulty of separation. By the study of comparing the reactivity with indolebetween asymmetric disulfide and symmetric disulfide compounds under the sameconditions, the result indicated that the reactivity of the asymmetric disulfidecomponds was lower.The fluorescence properties of IMP-N、BrIMP-N、BrIEP-N were studied, whichshowed good luminescent properties. All the above compounds were used asantifoulants in antifouling coatings, respectively. After an exposure to marineenvironment the coatings showed good antifouling activity. 2. Metal complexesThe molecular formulas and CCDC numbers of the two single-srystal complexesare listed as follows:[(Cu₂L₄（CH₄O）（H₂O）]·1/2CH₄O·H₂O（HL=2-furoic acid）; CCDC:921325C₃₄H₃₀Cu₂N₆O₆S₄·2（C₃H₇NO）; CCDC:911350The molecular structures of two single crystals were characterized by X-raysingle-crystal diffraction, showing that they both crystallized in slightly distortedoctahedral systems with space group P21/c and C2/c, respectively. The twocomplexes were further characterized by elemental analysis, IR spectroscopy andX-Ray Powder Diffraction.The fluorescence properties of the two single crystals were also studied, whichshowed good luminescent properties. In order to provide valuable theoretical supportfor the coordination principles and the stability of the complexes, the natural atomiccharges, the frontier molecular orbital energies and components of the two complexeswere calculated by the density functional theory （DFT） B3LYP method based on thecrystal data.