4081-35-0

Usage

Uses

Used in Coordination Chemistry:
N,N'-BIS(SALICYLIDENE)-1,6-HEXANEDIAMINE is used as a chelating ligand for forming stable complexes with metal ions, which is crucial for various applications in coordination chemistry.
Used in Catalysis:
In the field of catalysis, N,N'-BIS(SALICYLIDENE)-1,6-HEXANEDIAMINE is used as a ligand to create metal complexes that can act as catalysts, enhancing the rate of chemical reactions.
Used in Sensing:
N,N'-BIS(SALICYLIDENE)-1,6-HEXANEDIAMINE is used as a component in the development of sensing materials, where its metal complexes can be employed to detect specific analytes or ions.
Used in Material Science:
In material science, N,N'-BIS(SALICYLIDENE)-1,6-HEXANEDIAMINE is used in the synthesis of new materials with unique properties, such as metal-organic frameworks (MOFs) and other coordination polymers.
Used in Inorganic Chemistry Research:
N,N'-BIS(SALICYLIDENE)-1,6-HEXANEDIAMINE is utilized as a key component in inorganic chemistry research, where it helps in understanding the structure, bonding, and reactivity of metal complexes.

Upstream product

• 124-09-4 1,6-Hexanediamine 
• 90-02-8 salicylaldehyde 
• 89-95-2 2-methyl-benzyl alcohol 

Downstream Products

• 174911-66-1 Mn(C₂₀H₂₂N₂O₂)(H₂O)2⁽¹⁺⁾*B(C₆H₅)4^(1-)=[Mn(C₂₀H₂₂N₂O₂)(H₂O)2]B(C₆H₅)4 
• 2726-11-6 2,2′-[1,6-hexanediylbis(iminomethanediyl)]diphenol 

Relevant academic research and scientific papers

Enhanced luminescence for detection of small molecules based on doped lanthanide compounds with a dinuclear double-stranded helicate structure

A novel family of lanthanide materials with a dinuclear double-stranded helicate structure Ln2L2(DBM)4(OAc)2 [Ln = Sm (1), Eu (2) Gd (3) and Yb (4)] constructed from β-diketonate (DBM = dibenzoylmethanide) and an auxiliary ligand Schiff base (H2L = N,N′-bis(salicylidene)butane-1,6-diamine) was investigated. The structures of isostructural complexes 1-4 were determined by single-crystal and powder X-ray crystallography. The optical properties of these compounds could be enhanced by doping, allowing for doped materials with tunable visible and near-infrared emission. Subsequently, a multifunctional sensor was employed to detect CH3COOH, as well as the poisonous ions Al3+ and Cr2O72-. The notable quenching effect and luminescence-based color change showed that doped materials are promising fluorescence probes for the identification and detection of specific anions, cations and organic small molecules.

Enantiomeric bis(μ-N,N′-hexamethylenedisalicylaldiminato)dicopper(II) complexes

Dimeric complex, bis(μ-N,N′-hexa-methylenedisalicylaldiminato)-dicopper(II) was investigated using single crystal X-ray diffraction, thermogravimetric analysis, differential scanning calorimetry and Fourier transform infrared spectroscopy. The complex was

Spectroscopy study on the photochromism of Schiff bases N,N'-bis(salicylidene)-1,2-diaminoethane and N,N'-bis(salicylidene)-1,6-hexanediamine.

The photochromism of Schiff bases N,N'-bis(salicylidene)-1,2-diaminoethane (BSE) and N,N'-bis(salicylidene)-1,6-cyclohexanediamine (BSH) was studied by steady-state and time-dependent fluorescence, UV Vis absorption spectroscopy and theoretical chemistry calculations. The experimental results show that BSH can perform the photochromism easier than BSE, may be due to the molecular topology difference.

Titanium (IV) complexes of some tetra-dentate symmetrical bis-Schiff bases of 1,6-hexanediamine: Synthesis, characterization, and in silico prediction of potential inhibitor against coronavirus (SARS-CoV-2)

Symmetrical bis-Schiff bases (LH2) have been synthesized by the condensation of 1,6-hexanediamine (hn) and carbonyl or dicarbonyl. One of the synthesized Schiff bases has been subjected to the molecular docking for the prediction of their potentiality against coronavirus (SARS-CoV-2). Molecular docking revealed that tested Schiff base possessed high binding affinity with the receptor protein of SARS CoV-2 compared with hydroxychloroquine (HCQ). The ADMET analysis showed that ligand is non-carcinogenic and less toxic than standard HCQ. Schiff bases acting as dibasic tetra-dentate ligands formed titanium (IV) complexes of the type [TiL(H2O)2Cl2] or [TiL(H2O)2]Cl2 being coordinated through ONNO donor atoms. Ligands and complexes were characterized by the elemental analysis and physicochemical and spectroscopic data including FTIR, 1H NMR, mass spectra, UV-Visible spectra, molar conductance, and magnetic measurement. Optimized structures obtained from quantum chemical calculations supported the formation of complexes. Antibacterial, antifungal, and anti-oxidant activity assessments have been studied for synthesized ligands and complexes.

Synthesis, molecular modeling, and biomedical applications of oxovanadium(IV) complexes of Schiff bases as a good SARS-CoV-2 inhibitor

Oxovanadium(IV) complexes of dibasic symmetrical bis-Schiff bases synthesized from 1,6-hexanediamine and orthohydroxy aldehydes or diketones. Their formation was confirmed with the help of elemental analysis, FTIR, 1H NMR, UV-visible and mass spectra, magnetic susceptibility, and conductance measurements. Quantum mechanical calculations are indicative to the proposed structures of the complexes. Most of the ligands and complexes have considerable inhibition capacity on mycelia growth against selected pathogenic fungi and bacteria and show good antioxidant property too. Complexes showed good larvicidal activity against the mosquito larvae (Culex quinquefasciatus). Molecular docking of a Schiff base, (BzA-HD-BzAH2) with SARS-CoV-2 Mpro revealed the best binding affinity with the receptor protein compared to the approved medicine hydroxychloroquine (HCQ) and favipiravir (FVP). The ADMET analysis showed that ligand is non-carcinogenic and less toxic than standards, HCQ or FVP. However, these in silico studies proved BzA-HD-BzAH2 to be a good candidate for development as a therapeutic drug against SARS-CoV-2.

Influences of polarizability effect of alkyl group and homoring competition effect of substituents on the NMR spectra of salen-type Schiff base

Salen-type Schiff bases are a kind of important compounds and are widely used. In order to explore the effect of alkyl groups and substituents attached to aromatic ring on the chemical shifts, 63 title compounds were synthesized. Their 1H NMR and 13C NMR spectra were obtained; and the effects of the alkyl chain length and substituents on the chemical shifts (δH(CH=N), δC(CH=N), δH(OH), and δC(C-OH)) were studied. The results show that (1) the alkyl polarizability effect index (PEI) has an important influence on the chemical shifts of the above four atoms, with the increase of PEI, the values of δH(CH=N) and δc(CH=N) decrease, and the values of δH(OH) and δC(C-OH) increase. (2) The influence of substituent X attached to aromatic ring on the chemical shift is related to its position by taking OH or CH=N as reference. As for the effect of substituent on the chemical shifts, the effect of Hammett constant σ(X)-OH and excited-state substituent parameter (Formula presented.) with OH as reference are different from that ofσ(X)-CH=N and (Formula presented.) with CH=N as reference, and there is a “homoring competition effect” of the substituent. (3) The effect of the cross-interaction between X and OH on the chemical shift is also significantly different due to the different position of X. Quantitative correlation equations against chemical shifts were built for the four atoms, and the stability and prediction ability of the obtained equations were confirmed by leave-one-out cross validation.

Red Luminescent Eu(III) Coordination Bricks Excited on Blue LED Chip

Three types of red luminescent Eu(III) complexes with Schiff base and hfa ligands (hfa: hexafluoroacetylacetonate), mononuclear [Eu(hfa)2(OAc)(salen)2] (OAc: acetate anion, salen: N,N′-bis(salicylidene)ethylenediamine), brick-type [Eu2(hfa)4(OAc)2(salbn)2] (salbn: N,N′-bis(salicylidene)-1,4-butanediamine), and polynuclear [Eu(hfa)2(OAc)(salhen)]n (salhen: N,N′-bis(salicylidene)-1,6-hexanediamine) are reported for white light-emitting diode (LED) devices. Among these complexes, brick-type [Eu2(hfa)4(OAc)2(salbn)2] excited by blue light (460 nm) exhibits the photosensitized quantum yield (φπ-π? = 47%) and remarkably high efficiency of sensitization (ηsens = 96%). The efficiency of sensitization is caused by the excited state based on ligand-ligand interaction between the Schiff base and hfa ligands in Eu(III) complexes. To fabricate LED devices, the red luminescent [Eu2(hfa)4(OAc)2(salbn)2] was mounted on an InGaN blue LED chip.

Dioxovanadium(V) complexes of Schiff and tetrahydro-Schiff bases encapsulated in zeolite-Y for the aerobic oxidation of styrene

A series of dioxovanadium(V) complexes of Schiff and tetrahydro-Schiff bases were encapsulated into the supercages of zeolite-Y and were characterized by X-ray diffraction, SEM, N2 adsorption/desorption, FT-IR, UV-vis spectroscopy, ICPAES, pair distribution function (PDF) and X-ray absorption near edge structure (XANES) measurements. The encapsulation is achieved by a flexible ligand method in which the transition metal cations were first ion-exchanged into zeolite-Y and then complexed with ligands. The dioxovanadium-exchanged zeolite, dioxovanadium complexes encapsulated in zeolite-Y plus non-encapsulated homogeneous counterparts were all screened as catalysts for the aerobic oxidation of styrene under mild conditions. It was found that the encapsulated complexes showed better activity than their respective nonencapsulated counterparts in most cases. All encapsulated dioxovanadium tetrahydro-Schiff base complexes showed much higher activity in aerobic oxidation of styrene than their corresponding Schiff base complexes.

Functionalized Salen ligands linking with non-conjugated bridges: unique and colorful aggregation-induced emission, mechanism, and applications

A series of novel, simple, and colorful Salen ligands (56 samples), salicylaldehyde-based bis-Schiff bases, linking with different non-conjugated alkyl bridges ((CH2)n, n = 2-9, 12; cyclohexyl) and containing different electron-accepting (-NO2, -F, and -Cl), electron-donating (-OMe, -OH, and -NEt2), or sterically hindering (-t-butyl) substituents or a π-extended system (naphthalene ring) have been designed and synthesized. The photophysical properties of these Salen ligands can be well-tuned by the introduction of side functional substituents, π-extended systems, and central N-alkyl chain bridges. It is unusual that they contain a small π-conjugated system but display strong blue, green, and red aggregation-induced emission (AIE) with large Stokes shifts (up to 162 nm) and high fluorescence quantum yields (up to 0.44 and 0.75 in water and in solid, respectively). Combining with their advantages of AIE and good stability and biocompatibility, the Salen ligands can be potentially used in mechanofluorochromism (crystal-defect-induced emission) and living cell imaging. Moreover, the inherent relationships between their chemical structures and AIE properties are studied, which provide unequivocal insights for the design of AIE-active dyes.

Salen and tetrahydrosalen derivatives act as effective inhibitors of the tumor-associated carbonic anhydrase XII - A new scaffold for designing isoform-selective inhibitors

Salen and tetrahydrosalen derivatives possess metal-chelating properties and have been used as ligands in organic synthesis and as scaffolds for developing therapeutic agents. Fourteen such compounds were synthesized in order to explore their ability to inhibit the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1). Human (h) isoforms hCA I, hCA II, hCA IX and hCA XII were included in the investigation. Several aliphatic and aromatic spacers were introduced between the two chelating groups from salen/tetrahydrosalen in order to explore a diverse chemical space for designing CA inhibitors, which incorporate both phenol and polyamine fragments in their molecule. Some of these compounds showed CA inhibitory activity in the low micromolar-nanomolar range and a pronounced selectivity for inhibiting an isoform over-expressed in hypoxic tumors, hCA XII, over hCA I, II and IX.