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New Coordination Compounds of Cuii with Schiff Base Ligands—Crystal

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New Coordination Compounds of Cuii with Schiff Base Ligands—Crystal crystals Article New Coordination Compounds of CuII with Schiff Base Ligands—Crystal Structure, Thermal, and Spectral Investigations Dariusz Osypiuk , Beata Cristóvão and Agata Bartyzel * Department of General and Coordination Chemistry and Crystallography, Faculty of Chemistry, Institute of Chemical Sciences, Maria Curie-Sklodowska University in Lublin, Maria Curie-Sklodowska Sq. 2, 20-031 Lublin, Poland; [email protected] (D.O.); [email protected] (B.C.) * Correspondence: [email protected] Received: 19 October 2020; Accepted: 4 November 2020; Published: 5 November 2020 Abstract: The new mono-, di- and tetranuclear coordination compounds [Cu(HL1)] H O (1), · 2 [Cu (L1)(OAc)(MeOH)] 2H O MeOH (2), [Cu (L2) (OAc) ] 4MeOH (3), and [Cu (L2) (OAc) ] 4H O 2 · 2 · 4 2 2 · 4 2 2 · 2 4MeOH (4) were synthesized by the direct reaction of 2,20-{(2-hydroxypropane-1,3-diyl)bis · 1 [nitrilomethylidene]}bis(4-bromo-6-methoxyphenol) (H3L ) or 2,20-{(2-hydroxypropane-1,3-diyl)bis 2 (nitriloeth-1-yl-1-ylidene)}diphenol (H3L ) and the Cu(II) salt. They were characterized by elemental analysis, X-ray fluorescence (XRF), Fourier transform infrared (FTIR) spectroscopy, simultaneous thermal analysis and differential scanning calorimetry (TG/DSC), and thermal analysis coupled with Fourier transform infrared spectroscopy (TG-FTIR) techniques and the single crystal X-ray diffraction study. In the dinuclear complex 2, the copper(II) ions are bridged by an alkoxo- and a carboxylato bridges. The tetranuclear complexes 3 and 4 are formed from dinuclear species linkage through the phenoxo oxygen 2 atoms of the fully deprotonated H3L . Compounds 1–4 are stable at room temperature. During heating in air, at first, the solvent molecules (water and/or methanol) are lost and after that, the organic part undergoes defragmentation and combustion. The final decomposition solid product is CuO. The main gaseous products resulting from the thermal degradation of 1–4 in a nitrogen atmosphere were: H2O, MeOH, CH3COOH, CH4,C6H5OH, CO2, CO, and NH3. Keywords: Schiff base; N,O-donor ligand; complexes of Cu(II); crystal structure; thermal properties 1. Introduction The interest in the N,O-donor Schiff bases in the field of coordination chemistry has increased over the last several years because they can form stable coordination compounds with most transition metals [1–21]. These types of ligands and their complexes show interesting properties that can be potentially used in various fields such as catalysis [7–9], analytical chemistry [10,11], magnetic [5,6,12–15], and photoluminescence materials [4,16–19], etc. They also exhibit significant biological properties (e.g., antifungal, antibacterial, antimalarial, antiproliferative, anti-inflammatory, antiviral, and antioxidant [1,4,20–26]). We are interested in the synthesis of Schiff bases based on aromatic aldehydes or ketones with flexible diamines (e.g., 1,3-diaminopropane) and the study of their coordination ability toward transition metal ions. Most Schiff bases, formed in reaction of 1,3-diaminopropane with o-hydroxy aromatic aldehydes/ketones (Scheme1a), coordinate a single metal(II) ion in the N 2O2 tetradentate cavity (Scheme1b). The coordination environment of the metal ion consists of two oxygen and two nitrogen atoms of one Schiff base and occasionally, additional donor atoms derived from other molecules Crystals 2020, 10, 1004; doi:10.3390/cryst10111004 www.mdpi.com/journal/crystals Crystals 2020, 10, x FOR PEER REVIEW 2 of 21 Crystals 2020, 10, 1004 2 of 20 nitrogen atoms of one Schiff base and occasionally, additional donor atoms derived from other molecules (e.g., a solvent) are also present. Structures in which two metal ions are built into the cavity (e.g.,of the a solvent)above-mentioned are also present. derivatives Structures of the inSchiff which base two are metal very ions rare. are A built survey into of the the cavity Cambridge of the above-mentionedStructural Database derivatives (CSD version of the 5.41 Schi withff base updates are very August rare. 2020 A survey [27] revealed of the Cambridge that there Structuralis only one Databasecrystal structure (CSD version where two 5.41 metal(II) with updates ions are August incorporated 2020 [27 into] revealed the N2O that2 Schiff there base is only cavity. one This crystal type structureof complex where was twoobtained metal(II) by ionsLi et areal. incorporated(CSD code: OBEFUW into the N[227O,228Schi]) whereff base the cavity. Schiff This base type ligand of complexcoordinates was obtainedtwo Cd II byion Lis via et al. one (CSD azomethine code: OBEFUW nitrogen [27 and,28]) one where phenolate the Schi oxygenff base ligand atom (Scheme coordinates 1c). twoAdditionally Cd II ions, viathe one coordination azomethine sphere nitrogen of metal and one centers phenolate is supplemented oxygen atom by (Scheme two pyridine1c). Additionally, molecules. theAs coordinationa result, a metallo spheremacrocyclic of metal centersstructure is is supplemented formed. In the by case two of pyridine metal ions molecules. with a valenceAs a result, other athan metallomacrocyclic two, the above-mentionedstructure is type formed. of ligand In the can case also of coordinate metal ions two with metals a valence via N2 otherO2 donor than atoms two, theas depicted above-mentioned in Schemetype 1 (CSD of ligand codes: can HIYRIQ also coordinate [27] (Scheme two metals 1d) and via NABULAN2O2 donor [2 atoms7] and as HUWNIW depicted in[2 Scheme7], Scheme1 (CSD 1e). codes: HIYRIQ [ 27] (Scheme1d) and ABULAN [ 27] and HUWNIW [27], Scheme1e). Scheme 1. The N2O2-donor Schiff base ligands of 1,3-diaminopropane and o-hydroxy aromatic Scheme 1. The N2O2-donor Schiff base ligands of 1,3-diaminopropane and o-hydroxy aromatic ketones/aldehydes (a) and their possible coordination modes (b–e). ketones/aldehydes (a) and their possible coordination modes (b–e). In this paper, we present CuII complexes with similar types of ligands as depicted in Scheme2a. In this paper, we present CuII complexes with similar types of ligands as depicted in Scheme 2a. The Schiff bases contain an additional hydroxyl group, which enhances their ability to coordinate The Schiff bases contain an additional hydroxyl group, which enhances their ability to coordinate more than one metal ion (see Scheme2b–h and Table S1). According to the information found more than one metal ion (see Scheme 2b–h and Table S1). According to the information found in the in the CSD database, two types of copper(II) ions coordination are most common (i.e., one ion is CSD database, two types of copper(II) ions coordination are most common (i.e., one ion is coordinated coordinated in the N2O2 cavity of the Schiff base (Scheme2b) or when additional deprotonation in the N2O2 cavity of the Schiff base (Scheme 2b) or when additional deprotonation of the alcoholic of the alcoholic group occurs, two copper atoms are bound by N2O3 donor atoms of the ligand group occurs, two copper atoms are bound by N2O3 donor atoms of the ligand (Scheme 2c). (Scheme2c). Tetranuclear copper(II) complexes, where there is an additional oxygen atom either Tetranuclear copper(II) complexes, where there is an additional oxygen atom either from the (Scheme from the (Scheme2d) alkoxide or phenoxide (Scheme2e) group of the second Schi ff base in the 2d) alkoxide or phenoxide (Scheme 2e) group of the second Schiff base in the coordination coordination environment of the central ion, are also quite often observed. Structures with a mixed type environment of the central ion, are also quite often observed. Structures with a mixed type of of coordination (Scheme2g,h) are less common. Mukherjee et al. [ 29] synthesized cationic complexes coordination (Scheme 2g,h) are less common. Mukherjee et al. [29] synthesized cationic complexes consisting of a trinuclear copper(II) core (CSD codes: ILAPEQ [27] and ILAPIU [27]) where the consisting of a trinuclear copper(II) core (CSD codes: ILAPEQ [27] and ILAPIU [27]) where the coordination geometry of two terminal copper atoms was distorted square planar while the central ones coordination geometry of two terminal copper atoms was distorted square planar while the central had a distorted square-pyramidal. Yang and co-workers [30] also described a hexanuclear copper(II) ones had a distorted square-pyramidal. Yang and co-workers [30] also described a hexanuclear complex (Scheme2h). copper(II) complex (Scheme 2h). Crystals 20202020, 10, x 1004 FOR PEER REVIEW 33 of of 21 20 Crystals 2020, 10, x FOR PEER REVIEW 3 of 21 Scheme 2.2. GeneralGeneral depiction depiction of of the the structures structures that that bis o -hydroxybis o-hydroxy Schiff basesSchiff of base 1,3-diamino-2-propanols of 1,3-diamino-2- propanolandSchemeo-hydroxy and2. General o-hydroxy aromatic depiction aromatic ketones of/ aldehydesketones/aldehydes the structures adopt that with adopt bis copper(II) owith-hydroxy copper(II) ions: Schiff (a ions) iminebase: (as) ligand,imineof 1,3 -ligand,diamino (b–h) ( theb-–2- hpossiblepropanol) the possible coordination and ocoordination-hydroxy modes. aromatic modes. ketones/aldehydes adopt with copper(II) ions: (a) imine ligand, (b– h) the possible coordination modes. HereinHerein,, we report the crystal structures, thermal thermal,, and and spectral spectral properties properties of of four four new new Cu(II) Cu(II) SchiffSchiffHerein basebase complexes. complexes., we report In the Inthe the researchcrystal research, structures,, we used we used two thermal Schiff two, Schi andbasesff spectral basesas ligands as properties ligands that differ that ofed four di inff the erednew amount inCu(II) the andamountSchiff kind base and complexes.of kind substituents of substituents In the researchin inthe the , webenzene benzene used two ringring Schiff (Scheme (Scheme bases3 ).as 2,2ligands3).0 -{(2-hydroxypropane-1,3-diyl)2,2’ that-{(2- differhydroxypropaneed in the amount-1,3- 1 diyl)bis[nitrilomethylidene]}bis(4bis[nitrilomethylidene]}bis(4-bromo-6-methoxyphenol)and kind of substituents in- bromothe benzene-6-methoxyphenol) ring H(Scheme3L H, possessing3L1 , possessing3).
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