Microwave-assisted synthesis and mesomorphic investigations of p-substituted aroylhydrazones and their nickel(II) and copper(II) complexes

The present study is focused on the development of green microwave process for the synthesis of mesogenic substituted aroylhydrazones and their nickel(II) and copper(II) complexes. The compounds have been synthesised by microwave-assisted as well as thermal methods for comparison purpose. The compounds were structurally characterised by using suitable spectroscopic techniques. The mesomorphic properties were studied by differential scanning calorimetric analysis and polarising optical microscopy. The stable molecular structures of the mesogenic methylidenehydrazinato-nickel(II) complex have been obtained by density functional theoretical method to understand the structural origin responsible for the mesomorphic property.

[1]  Bachchan Singh,et al.  Synthesis, characterization and mesomorphic investigations of ester-substituted aroylhydrazones possessing a lateral hydroxyl group , 2014 .

[2]  Bachchan Singh,et al.  Synthesis and mesomorphic investigation of calamitic liquid crystalline system ethyl-[4-(4′-decyloxy)benzoyloxy]-benzoate (4-EDBB): A temperature dependent micro-Raman study and DFT calculations , 2013 .

[3]  S. Teat,et al.  Microwave assisted synthesis in coordination chemistry , 2013 .

[4]  Bachchan Singh,et al.  Synthesis, characterisation and mesomorphic properties of ester containing aroylhydrazones and their nickel(II) complexes , 2011 .

[5]  Weisheng Liu,et al.  Aroylhydrazone derivative as fluorescent sensor for highly selective recognition of Zn2+ ions: syntheses, characterization, crystal structures and spectroscopic properties. , 2011, Dalton transactions.

[6]  K. Vávrová,et al.  Synthesis and initial in vitro evaluations of novel antioxidant aroylhydrazone iron chelators with increased stability against plasma hydrolysis. , 2011, Chemical research in toxicology.

[7]  T. White,et al.  Light-driven nanoscale chiral molecular switch: reversible dynamic full range color phototuning. , 2010, Chemical communications.

[8]  D. Gin,et al.  New type of Li ion conductor with 3D interconnected nanopores via polymerization of a liquid organic electrolyte-filled lyotropic liquid-crystal assembly. , 2009, Journal of the American Chemical Society.

[9]  Adrian-Mihail Stadler,et al.  Bis-acyl-/aroyl-hydrazones as multidentate ligands , 2009 .

[10]  Serguei P. Palto,et al.  Cholesteric helix: topological problem, photonics and electro-optics , 2009 .

[11]  Sandeep Kumar,et al.  Room-temperature electron-deficient discotic liquid crystals: facile synthesis and mesophase characterization , 2008 .

[12]  Xiao‐Hui Liu,et al.  Synthesis, characterization, and DNA-binding properties of the cobalt(II) and nickel(II) complexes with salicylaldehyde 2-phenylquinoline-4-carboylhydrazone , 2008 .

[13]  Xiao‐Hui Liu,et al.  Synthesis, characterization, and DNA-binding properties of copper(II), cobalt(II), and nickel(II) complexes with salicylaldehyde 2-phenylquinoline-4-carboylhydrazone , 2008 .

[14]  K. Stadnicka,et al.  Iron(III) complexes with a biologically relevant aroylhydrazone: crystallographic evidence for coordination versatility. , 2007, Inorganic chemistry.

[15]  W. Haase,et al.  Metal complexes derived from hydrazoneoxime ligands: III – Synthesis, characterization and electrospray ionization mass spectra of some nickel(II) complexes with aroylhydrazoneoximes ☆ , 2007 .

[16]  F. Sarkar,et al.  Novel Schiff base copper complexes of quinoline-2 carboxaldehyde as proteasome inhibitors in human prostate cancer cells. , 2006, Journal of medicinal chemistry.

[17]  D. Richardson,et al.  Complexes of cytotoxic chelators from the dipyridyl ketone isonicotinoyl hydrazone (HPKIH) analogues. , 2006, Inorganic chemistry.

[18]  R. Lemieux Photoswitching of ferroelectric liquid crystals using photochromic dopants. , 2005, Soft matter.

[19]  C. Kappe,et al.  Controlled microwave heating in modern organic synthesis. , 2004, Angewandte Chemie.

[20]  Ulrich S. Schubert,et al.  Microwave-Assisted Polymer Synthesis: State-of-the-Art and Future Perspectives , 2004 .

[21]  S. D. Hudson,et al.  Self-assembly of amphiphilic dendritic dipeptides into helical pores , 2004, Nature.

[22]  Werner Bonrath,et al.  Microwave assisted synthesis – a critical technology overview , 2004 .

[23]  A. Boudenne,et al.  Temperature and liquid crystal concentration effect on thermal conductivity of poly(styrene) dispersed 5CB liquid crystal , 2003 .

[24]  Noel A. Clark,et al.  Electrostatics and the electro-optic behaviour of chiral smectics C: 'block' polarization screening of applied voltage and 'V-shaped' switching , 2000 .

[25]  A. Bacchi,et al.  Correlated columnar phases: aroylhydrazinato nickel(II) complexes as novel discotics , 1999 .

[26]  F. Simoni Non-linear optics in liquid crystals: basic ideas and perspectives , 1998 .

[27]  Chung K. Lai,et al.  Discotic metallomesogens: mesophase crossover of columnar rectangular to hexagonal arrangements in bis(hydrazinato)nickel(II) complexes , 1998 .

[28]  E. Dalcanale,et al.  Nickel(II) Complexes of 2, 6-Disubstituted Pyridine Bishydrazones as Potential Metallomesogens. Suppression of the Mesogenic Properties Induced by Dimerization , 1998 .

[29]  Leo Radom,et al.  Harmonic Vibrational Frequencies: An Evaluation of Hartree−Fock, Møller−Plesset, Quadratic Configuration Interaction, Density Functional Theory, and Semiempirical Scale Factors , 1996 .

[30]  J. Serrano Metallomesogens : synthesis, properties, and applications , 1996 .

[31]  Z. Galewski Liquid Crystalline Properties of 4-Alkoxy-Aniline-4′-Alkoxy-Anilines , 1994 .

[32]  S. Jayasree,et al.  SYNTHESIS AND PHYSICOCHEMICAL INVESTIGATION OF METAL COMPLEXES WITH HYDRAZONE AND ISONICOTINOYLHYDRAZONE OF ACETOACETANILIDE , 1994 .

[33]  M. C. Holmes,et al.  Examination of the structural features necessary for mesophase formation with aroylhydrazinato-nickel(II) and -copper(II) complexes , 1994 .

[34]  Sakurai,et al.  Thermal conductivity of the nematic liquid crystal 4-n-pentyl-4'-cyanobiphenyl. , 1994, Physical review. E, Statistical physics, plasmas, fluids, and related interdisciplinary topics.

[35]  M. C. Holmes,et al.  Aroylhydrazinatonickel(II) and copper(II) complexes; a new class of metallomesogens , 1993 .

[36]  J. Dance,et al.  Magnetic and esr study of a dimeric copper(II) complex with a schiff base ligand derived from salicylhydrazide and o-hydroxypropiophenone , 1988 .

[37]  J. Simon,et al.  Synthesis and study of the mesomorphism of highly polarizable mesogens towards applications in non-linear optics , 1987 .

[38]  L. Pickart,et al.  Cytotoxic chelators and chelates 1. Inhibition of DNA synthesis in cultured rodent and human cells by aroylhydrazones and by a copper(II) complex of salicylaldehyde benzoyl hydrazone , 1982 .

[39]  M. Valcárcel,et al.  Pyridine-2-carbaldehyde 2-hydroxybenzoylhydrazone as a selective reagent for the extraction and spectrophotometric determination of iron(II) , 1979 .