Theoretical investigation of the structural and electronic properties of molecular machine based on phenylene and trityl

South African Journal of Chemical Engineering - Tập 37 - Trang 237-243 - 2021
Tiyam Molaaghaei1, Khadijeh Kalateh1, Jamshid Najafpour1, Roya Ahmadi1
1Department of Chemistry, College of Basic Sciences, Yadegar-e-Imam Khomeini (RAH) Shahre Rey Branch, Islamic Azad University, Tehran, Iran

Tài liệu tham khảo

Feynman, 1960, There's plenty of room at the bottom, Calif. Inst. Technol., Eng. Sci. Magaz. Feynman, 1965, The feynman lectures on physics; vol. i, Am. J. Phys., 33, 750, 10.1119/1.1972241 Balzani, 2000, Artificial molecular machines, Angewand. Chemi.. Int. Edit., 39, 3348, 10.1002/1521-3773(20001002)39:19<3348::AID-ANIE3348>3.0.CO;2-X Kottas, 2005, Artificial molecular rotors, Chem. Rev., 105, 1281, 10.1021/cr0300993 Boskovic, 2016, Kinematic molecular manufacturing machines, Coord. Chem. Rev., 329, 163, 10.1016/j.ccr.2016.09.007 Kay, 2007, Synthetic molecular motors and mechanical machines, Angewand. Chemi. Int. Edit., 46, 72 Martinez-Bulit, 2019, Rotors, motors, and machines inside metal–organic frameworks, Trend. Chem., 10.1016/j.trechm.2019.05.005 Sluysmans, 2018, Growing community of artificial molecular machinists, Proceed. Nat. Acad. Sci., 115, 9359, 10.1073/pnas.1813973115 Sluysmans, 2019, The burgeoning of mechanically interlocked molecules in chemistry, Trend. Chem., 10.1016/j.trechm.2019.02.013 Garcia-Garibay, 2005, Crystalline molecular machines: encoding supramolecular dynamics into molecular structure, Proceed. Nat. Acad. Sci., 102, 10771, 10.1073/pnas.0502816102 Feringa, 2017, The art of building small: from molecular switches to motors (nobel lecture), Angewand. Chemi. Int. Edit., 56, 11060, 10.1002/anie.201702979 Sauvage, 2017, From chemical topology to molecular machines (nobel lecture), Angewand. Chemi. Int.l Edit., 56, 11080, 10.1002/anie.201702992 Leigh, 2016, Genesis of the nanomachines: the 2016 nobel prize in chemistry, Angewand. Chemi. Int. Edit., 55, 14506, 10.1002/anie.201609841 Baroncini, 2018, Making and operating molecular machines: a multidisciplinary challenge, ChemistryOp., 7, 169, 10.1002/open.201700181 Abendroth, 2015, Controlling motion at the nanoscale: rise of the molecular machines, ACS. Nano, 9, 7746, 10.1021/acsnano.5b03367 Kinbara, 2005, Toward intelligent molecular machines: directed motions of biological and artificial molecules and assemblies, Chem. Rev., 105, 1377, 10.1021/cr030071r Piccolino, 2000, Biological machines: from mills to molecules, Nat. Rev. Molecul. Cell Biol., 1, 149, 10.1038/35040097 Urry, 1993, Molecular machines: how motion and other functions of living organisms can result from reversible chemical changes, Angewand. Chemi. Int. Edit. Engl., 32, 819, 10.1002/anie.199308191 Amrute-Nayak, 2010, Targeted optimization of a protein nanomachine for operation in biohybrid devices, Angewand. Chemi. Int. Edit., 49, 312, 10.1002/anie.200905200 Gaudillière, 2000, Rockefeller strategies for scientific medicine: molecular machines, viruses and vaccines, Studi. Hist. Philos. Sci. Part C: Studi. Hist. Philos. Biologi. Biomed. Sci., 31, 491 Sokolov, 2017, Smart materials on the way to theranostic nanorobots: molecular machines and nanomotors, advanced biosensors, and intelligent vehicles for drug delivery, Biochimica et Biophysica Acta (BBA) - Gener. Subj., 1861, 1530, 10.1016/j.bbagen.2017.01.027 Patel, 2006, Nanorobot: a versatile tool in nanomedicine, J. Drug Target., 14, 63, 10.1080/10611860600612862 Balasubramanian, 2011, Micromachine-enabled capture and isolation of cancer cells in complex media, Angewand. Chemi. Int. Edit., 50, 4161, 10.1002/anie.201100115 Li, 2019, Stimuli-Responsive drug-delivery systems based on supramolecular nanovalves, Matt., 1, 345, 10.1016/j.matt.2019.05.019 Angelos, 2008, Mesoporous silicate materials as substrates for molecular machines and drug delivery, Chem. Eng. J., 137, 4, 10.1016/j.cej.2007.07.074 García-López, 2017, Molecular machines open cell membranes, Nat., 548, 567, 10.1038/nature23657 Goltry, 2015, DNA topology influences molecular machine lifetime in human serum, Nanosc., 7, 10382, 10.1039/C5NR02283E Ariga, 2014, Bioinspired nanoarchitectonics as emerging drug delivery systems, J. Chem., 38, 5149 Ariga, 2016, Molecular cavity nanoarchitectonics for biomedical application and mechanical cavity manipulation, CrystEngComm., 18, 4890, 10.1039/C6CE00432F Xuan, 2014, Self-propelled janus mesoporous silica nanomotors with sub-100 nm diameters for drug encapsulation and delivery, ChemPhysChem., 15, 2255, 10.1002/cphc.201402111 Yuan, 2018, Chaperonin-GroEL as a smart hydrophobic drug delivery and tumor targeting molecular machine for tumor therapy, Nano Lett., 18, 921, 10.1021/acs.nanolett.7b04307 Selis, 2019, Nano-machine to nano-machine molecular communications for drug delivery systems, Proceed. Sixth Annu. ACM Int. Confer. Nanosc. Computi. Commun., 10.1145/3345312.3345471 Chen, 2019, Nanomachines and other caps on mesoporous silica nanoparticles for drug delivery, Acc. Chem. Res., 10.1021/acs.accounts.9b00116 Skopek, 2007, Gyroscopes and the chemical literature: 1852–2002, Coord Chem Rev, 251, 1723, 10.1016/j.ccr.2006.12.015 Lang, 2016, Gyroscope-like complexes based on dibridgehead diphosphine cages that are accessed by three-fold intramolecular ring closing metatheses and encase fe (co) 3, fe (co) 2 (no)+, and fe (co) 3 (h)+ rotators, J. Am. Chem. Soc., 138, 7649, 10.1021/jacs.6b03178 Marsella, 2007, Molecular springs, muscles, rheostats, and precessing gyroscopes: from review to preview, Org. Biomol. Chem., 5, 391, 10.1039/b613891h Prack, 2015, A molecular rotor possessing an h–m–h “spoke” on a p–m–p “axle”: a platinum (ii) trans-dihydride spins rapidly even at 75 k, J. Am. Chem. Soc., 137, 13464, 10.1021/jacs.5b08213 Taher, 2016, Mono-and disubstitution reactions of gyroscope like complexes derived from clptcl rotators within cage like dibridgehead diphosphine ligands, J Organomet. Chem., 821, 136, 10.1016/j.jorganchem.2016.03.022 Lang, 2016, Syntheses, reactivity, structures, and dynamic properties of gyroscope-like iron carbonyl complexes based on dibridgehead diarsine cages, Organomet., 35, 2873, 10.1021/acs.organomet.6b00447 Li, 2017, Crystalline supramolecular gyroscope with a water molecule as an ultrasmall polar rotator modulated by charge-assisted hydrogen bonds, J. Am. Chem. Soc., 139, 8086, 10.1021/jacs.7b02981 Fiedler, 2016, Gyroscope like molecules consisting of trigonal or square planar osmium rotators within three-spoked dibridgehead diphosphine stators: syntheses, substitution reactions, structures, and dynamic properties, Dalt. Trans., 45, 7131, 10.1039/C6DT00692B Dominguez, 2002, Molecular “compasses” and “gyroscopes”. i. expedient synthesis and solid state dynamics of an open rotor with a bis (triarylmethyl) frame, J. Am. Chem. Soc., 124, 2398, 10.1021/ja0119447 Godinez, 2002, Molecular compasses and gyroscopes. ii. synthesis and characterization of molecular rotors with axially substituted bis [2-(9-triptycyl) ethynyl] arenes, J. Am. Chem. Soc., 124, 4701, 10.1021/ja012550i Dominguez, 2002, Molecular “compasses” and “gyroscopes.” iii. dynamics of a phenylene rotor and clathrated benzene in a slipping-gear crystal lattice, J. Am. Chem. Soc., 124, 7719, 10.1021/ja025753v Dominguez, 2003, Molecular compasses and gyroscopes with polar rotors: synthesis and characterization of crystalline forms, J. Am. Chem. Soc., 125, 8827, 10.1021/ja035274b Santillán, 2008, Synthesis and characterization of natural abundance and isotopically labeled 1, 4-bis (3, 3, 3-triphenylpropynyl)-2, 3-difluorobenzene: a molecular gyroscope with a polar rotator, J. Mex .Chem. Soc., 52, 125 Horansky, 2005, Dielectric response of a dipolar molecular rotor crystal, Physic. Rev. B, 72, 10.1103/PhysRevB.72.014302 Godinez, 2004, Molecular crystals with moving parts: synthesis, characterization, and crystal packing of molecular gyroscopes with methyl-substituted triptycyl frames, J. Org. Chem., 69, 1652, 10.1021/jo035517i Nuñez, 2006, Crystal phases and phase transitions in a highly polymorphogenic solid-state molecular gyroscope with m eta-methoxytrityl frames, Cryst. Grow. Des., 6, 866, 10.1021/cg050155o Khuong, 2007, Rotational dynamics in a crystalline molecular gyroscope by variable-temperature 13c nmr, 2h nmr, x-ray diffraction, and force field calculations, J. Am. Chem. Soc., 129, 839, 10.1021/ja064325c Nunez, 2007, Synthesis of a triply-bridged molecular gyroscope by a directed meridional cyclization strategy, Org. Lett., 9, 3559, 10.1021/ol071379y O’Brien, 2011, Synthesis and solid-state rotational dynamics of molecular gyroscopes with a robust and low density structure built with a phenylene rotator and a tri (meta-terphenyl) methyl stator, Cryst. Grow. Des., 11, 2654, 10.1021/cg200373g Jiang, 2016, Crystal fluidity reflected by fast rotational motion at the core, branches, and peripheral aromatic groups of a dendrimeric molecular rotor, J. Am. Chem. Soc., 138, 4650, 10.1021/jacs.6b01398 Karlen, 2005, Effects of rotational symmetry order on the solid state dynamics of phenylene and diamantane rotators, J. Am. Chem. Soc., 127, 6554, 10.1021/ja042512+ Akimov, 2011, Molecular dynamics study of crystalline molecular gyroscopes, J. Physic. Chem. C, 115, 13584, 10.1021/jp201981v Karlen, 2006, Crystalline molecular gyroscopes: the effects of subtle molecular differences on the crystal packing of triphenylmethyl and triphenylsilyl stators, Molecul. Cryst. Liq. Cryst., 456, 221, 10.1080/15421400600788757 Howe, 2019, The roles of intrinsic barriers and crystal fluidity in determining the dynamics of crystalline molecular rotors and molecular machines, J. Org. Chem., 84, 9835, 10.1021/acs.joc.9b00993 Karlen, 2006, Improved physical properties and rotational dynamics in a molecular gyroscope with an asymmetric stator structure, Org. Lett., 8, 3417, 10.1021/ol060894d Karlen, 2005, Highlighting gyroscopic motion in crystals in 13c cpmas spectra by specific isotopic substitution and restricted cross polarization, Chem. Commun., 189, 10.1039/b409744k Jiang, 2014, Rotation of a bulky triptycene in the solid state: toward engineered nanoscale artificial molecular machines, J. Am. Chem. Soc., 136, 8871, 10.1021/ja503467e Garcia-Garibay, 2009, Engineering crystal packing and internal dynamics in molecular gyroscopes by refining their components. fast exchange of a phenylene rotator by 2h nmr, Cryst. Grow. Des., 9, 3124, 10.1021/cg801065a Wan, 2018, Spin-Dependent transport properties of a phenylene rotor bridging carbon chains between graphene electrodes, Commun. Comput. Phys., 23, 781, 10.4208/cicp.OA-2017-0062 Marahatta, 2012, Theoretical investigation of the structures and dynamics of crystalline molecular gyroscopes, J. Physic. Chem. C, 116, 24845, 10.1021/jp308974j Frisch, 2004, 4 Becke, 1993, Density-functional thermochemistry. iii. the role of exact exchange, J. Chem. Phys., 98, 5648, 10.1063/1.464913 Lee, 1988, Development of the colle-salvetti correlation-energy formula into a functional of the electron density, Physic. Re. B, 37, 785, 10.1103/PhysRevB.37.785 Binkley, 1980, Self-consistent molecular orbital methods. 21. small split-valence basis sets for first-row elements, J. Am. Chem. Soc., 102, 939, 10.1021/ja00523a008 Kurban, 2019, Experimental and theoretical studies of the structural, electronic and optical properties of bczvb organic material, Optik (Stuttg), 182, 611, 10.1016/j.ijleo.2019.01.080 Tanış, 2018, The structural, electronic and spectroscopic properties of 4fpbape molecule: experimental and theoretical study, J. Mol. Struct., 1154, 301, 10.1016/j.molstruc.2017.10.057