Research Article
Year 2020,
Volume: 41 Issue: 2, 344 - 350, 25.06.2020
Abstract
References
- [1] Barnes J.C., Juricek M., Vermeulen N.A., Dale E.J. and Stoddart J.F., Synthesis of ExnBox Cyclophanes. J. Org. Chem., 78 (2013) 11962-11969.
- [2] Dale E.J., Vermeulen N.A., Juricek M., Barnes J.C., Young R.M., Wasielewski M.R. and Stoddart J.F., Supramolecular Explorations: Exhibiting the Extent of Extended Cationic Cyclophanes. Acc. Chem. Res., 49 (2016) 262-273.
- [3] Dale E.J., Ferris D.P., Vermeulen N.A., Hanklis J.J., Popovs I., Juricek M., Barnes J.C., Schneebeli S.T. and Stoddart J.F., Cooperative Reactivity in an Extended-Viologen-Based Cyclophane. J. Am. Chem. Soc., 138 (2016) 3667-3670.
- [4] Fang Q.-S., Chen L. and Liu Q.-L., Template-directed synthesis of pyridazine-containing tetracationic cyclophane for construction of [2] rotaxane. Chinese Chemical Letters 28 (2017) 1013-1017.
- [5] Mashraqui S.H., Sangvikar Y.S., Ghadigaonkar S.G., Ashraf M. and Meetsma M., Oxa-bridged cyclophanes featuring thieno[2,3-b]thiopheneand C2-symmetric binol or bis-naphthol rings:synthesis, structures, and conformational studies. Tetrahedron 64 (2008) 8837-8842.
- [6] Giancarlo L.C. and Flynn G.W., Raising Flags: Applications of Chemical Marker Groups To Study Self-Assembly, Chirality, and Orientation of Interfacial Films by Scanning Tunneling Microscopy. Acc. Chem. Res. 33 (2000) 491-501.
- [7] Asakawa M., Ashton P.R., Menzer S., Raymo F.M., Stoddart J.F., White A.J.P. and Williams D.J., Cyclobis(Paraquat‐4,4′‐Biphenylene)–an Organic Molecular Square. Chem. Eur. J., 2 (1996) 877-893.
- [8] Barnes J.C., Juríček M., Strutt N.L., Frasconi M., Sampath S., Giesener M.A., McGrier P.L., Bruns C.J., Stern C.L., Sarjeant A.A. and Stoddart J.F., ExBox: A Polycyclic Aromatic Hydrocarbon Scavenger. J. Am. Chem. Soc., 135 (2013) 183-192.
- [9] Juríček M., Barnes J.C., Dale E.J., Liu W.-G., Strutt N.L., Bruns C.J., Vermeulen N.A., Ghooray K., Sarjeant A.A., Stern C.L., Botros Y.Y., Goddard W.A. III and Stoddart J.F., Ex2Box: Interdependent Modes of Binding in a Two-Nanometer-Long Synthetic Receptor. J. Am. Chem. Soc., 135 (2013) 12736-12746.
- [10] Asakawa M., Dehaen W., L’abbe G.L., Menzer S., Nouwen J., Raymo F. M., Stoddart J. F. and Williams D.J., Omproved Template-Directed Synthesis of Cyclobis(paraquat-p-phenylene). J. Org. Chem., 61 (1996) 9591-9595.
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- [12] Gaussian 09, Revision D.01, Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Scalmani G., Barone V., Petersson G. A., Nakatsuji H., Li X., Caricato M., Marenich A. V., Bloino J., Janesko B.G., Gomperts R., Mennucci B., Hratchian H. P., Ortiz J. V., Izmaylov A. F., Sonnenberg J. L., Williams-Young D., Ding F., Lipparini F., Egidi F., Goings J., Peng B., Petrone A., Henderson T., Ranasinghe D., Zakrzewski V. G., Gao J., Rega N., Zheng G., Liang W., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Throssell K., Montgomery J.A. Jr., Peralta J. E., Ogliaro F., Bearpark M.J., Heyd J.J., Brothers E.N., Kudin K.N., Starovero, V.N., Keith T.A., Kobayashi R., Normand J., Raghavachari K., Rendell A.P., Burant J.C., Iyengar S.S., Tomasi J., Cossi M., Millam J.M., Klene M., Adamo C., Cammi R., Ochterski J.W., Martin R.L., Morokuma K., Farkas O., Foresman J. B. and Fox D. J. Gaussian, Inc., Wallingford CT, (2009).
- [13] PerkinElmer, ChemBioDraw Ultra Version (13.0.0.3015), CambridgeSoft Waltham, MA, USA (2012).
- [14] O'Boyle N.M., Tenderholt A.L. and Langner K.M.: cclib: A library for package‐independent computational chemistry algorithms. J Comp Chem, 29 (2008) 839-845.
- [15] Koopmans T., Über die Zuordnung von Wellenfunktionen und Eigenwerten zu den Einzelnen Elektronen Eines Atoms. Physica, 1 (1934) 104-113.
- [16] Tüzün B. and Sayin K., Investigations over optical properties of boron complexes of benzothiazolines. Spectrochim. Acta A, 208 (2019) 48-46.
- [17] Uludag N. and Serdaroğlu G., An improved synthesis, spectroscopic (FT-IR, NMR) study and DFT computational analysis (IR, NMR, UVeVis, MEP diagrams, NBO, NLO, FMO) of the 1,5-methanoazocino[4,3-b]indole core structure. J. Mol. Struct., 1155 (2018) 548-560.
- [18] Sayin K., Kariper S.E., Tas M., Alagoz Sayin T. and Karakas D., Investigations of structural, spectral, electronic and biological properties of N-heterocyclic carbene Ag(I) and Pd(II) complexes. J. Mol. Struct., 1176 (2019) 478-487.
- [19] Gungor S.A., Sahin I., Gungor O., Kariper S.E., Tumer F. and Kose M., Pamoic acid esters and their xanthene derivatives: Flourimetric detection of nitroaromatic compounds and non-linear optical properties. Sensors and Actuators B: Chemical, 255 (2018) 3344-3354.
Year 2020,
Volume: 41 Issue: 2, 344 - 350, 25.06.2020
Abstract
Modelling studies on some ExnBox Cyclophanes were performed at HF/6-31G(d) level. Structural properties are examined in detail. Density of state (DOS) spectrum and molecular orbital energy diagram of related compounds at ground state were calculated and contour plots of significant molecular orbitals were investigated in detail. Some quantum chemical descriptors were calculated in the gas phase to examine the non-linear optical properties. Finally, UV-VIS spectrum of the mentioned compounds was calculated and examined in gas phase, toluene, chloroform, ethanol, methanol, 1,2-ethanediol, water and n-methylformamide-mixture. As a result, EX2.2Box4+ was found as the best candidate to NLO applications.
References
- [1] Barnes J.C., Juricek M., Vermeulen N.A., Dale E.J. and Stoddart J.F., Synthesis of ExnBox Cyclophanes. J. Org. Chem., 78 (2013) 11962-11969.
- [2] Dale E.J., Vermeulen N.A., Juricek M., Barnes J.C., Young R.M., Wasielewski M.R. and Stoddart J.F., Supramolecular Explorations: Exhibiting the Extent of Extended Cationic Cyclophanes. Acc. Chem. Res., 49 (2016) 262-273.
- [3] Dale E.J., Ferris D.P., Vermeulen N.A., Hanklis J.J., Popovs I., Juricek M., Barnes J.C., Schneebeli S.T. and Stoddart J.F., Cooperative Reactivity in an Extended-Viologen-Based Cyclophane. J. Am. Chem. Soc., 138 (2016) 3667-3670.
- [4] Fang Q.-S., Chen L. and Liu Q.-L., Template-directed synthesis of pyridazine-containing tetracationic cyclophane for construction of [2] rotaxane. Chinese Chemical Letters 28 (2017) 1013-1017.
- [5] Mashraqui S.H., Sangvikar Y.S., Ghadigaonkar S.G., Ashraf M. and Meetsma M., Oxa-bridged cyclophanes featuring thieno[2,3-b]thiopheneand C2-symmetric binol or bis-naphthol rings:synthesis, structures, and conformational studies. Tetrahedron 64 (2008) 8837-8842.
- [6] Giancarlo L.C. and Flynn G.W., Raising Flags: Applications of Chemical Marker Groups To Study Self-Assembly, Chirality, and Orientation of Interfacial Films by Scanning Tunneling Microscopy. Acc. Chem. Res. 33 (2000) 491-501.
- [7] Asakawa M., Ashton P.R., Menzer S., Raymo F.M., Stoddart J.F., White A.J.P. and Williams D.J., Cyclobis(Paraquat‐4,4′‐Biphenylene)–an Organic Molecular Square. Chem. Eur. J., 2 (1996) 877-893.
- [8] Barnes J.C., Juríček M., Strutt N.L., Frasconi M., Sampath S., Giesener M.A., McGrier P.L., Bruns C.J., Stern C.L., Sarjeant A.A. and Stoddart J.F., ExBox: A Polycyclic Aromatic Hydrocarbon Scavenger. J. Am. Chem. Soc., 135 (2013) 183-192.
- [9] Juríček M., Barnes J.C., Dale E.J., Liu W.-G., Strutt N.L., Bruns C.J., Vermeulen N.A., Ghooray K., Sarjeant A.A., Stern C.L., Botros Y.Y., Goddard W.A. III and Stoddart J.F., Ex2Box: Interdependent Modes of Binding in a Two-Nanometer-Long Synthetic Receptor. J. Am. Chem. Soc., 135 (2013) 12736-12746.
- [10] Asakawa M., Dehaen W., L’abbe G.L., Menzer S., Nouwen J., Raymo F. M., Stoddart J. F. and Williams D.J., Omproved Template-Directed Synthesis of Cyclobis(paraquat-p-phenylene). J. Org. Chem., 61 (1996) 9591-9595.
- [11] Dennington II R.D., Keith T.A. and Millam J.M., GaussView 5.0, Wallingford, CT (2009).
- [12] Gaussian 09, Revision D.01, Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Scalmani G., Barone V., Petersson G. A., Nakatsuji H., Li X., Caricato M., Marenich A. V., Bloino J., Janesko B.G., Gomperts R., Mennucci B., Hratchian H. P., Ortiz J. V., Izmaylov A. F., Sonnenberg J. L., Williams-Young D., Ding F., Lipparini F., Egidi F., Goings J., Peng B., Petrone A., Henderson T., Ranasinghe D., Zakrzewski V. G., Gao J., Rega N., Zheng G., Liang W., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Throssell K., Montgomery J.A. Jr., Peralta J. E., Ogliaro F., Bearpark M.J., Heyd J.J., Brothers E.N., Kudin K.N., Starovero, V.N., Keith T.A., Kobayashi R., Normand J., Raghavachari K., Rendell A.P., Burant J.C., Iyengar S.S., Tomasi J., Cossi M., Millam J.M., Klene M., Adamo C., Cammi R., Ochterski J.W., Martin R.L., Morokuma K., Farkas O., Foresman J. B. and Fox D. J. Gaussian, Inc., Wallingford CT, (2009).
- [13] PerkinElmer, ChemBioDraw Ultra Version (13.0.0.3015), CambridgeSoft Waltham, MA, USA (2012).
- [14] O'Boyle N.M., Tenderholt A.L. and Langner K.M.: cclib: A library for package‐independent computational chemistry algorithms. J Comp Chem, 29 (2008) 839-845.
- [15] Koopmans T., Über die Zuordnung von Wellenfunktionen und Eigenwerten zu den Einzelnen Elektronen Eines Atoms. Physica, 1 (1934) 104-113.
- [16] Tüzün B. and Sayin K., Investigations over optical properties of boron complexes of benzothiazolines. Spectrochim. Acta A, 208 (2019) 48-46.
- [17] Uludag N. and Serdaroğlu G., An improved synthesis, spectroscopic (FT-IR, NMR) study and DFT computational analysis (IR, NMR, UVeVis, MEP diagrams, NBO, NLO, FMO) of the 1,5-methanoazocino[4,3-b]indole core structure. J. Mol. Struct., 1155 (2018) 548-560.
- [18] Sayin K., Kariper S.E., Tas M., Alagoz Sayin T. and Karakas D., Investigations of structural, spectral, electronic and biological properties of N-heterocyclic carbene Ag(I) and Pd(II) complexes. J. Mol. Struct., 1176 (2019) 478-487.
- [19] Gungor S.A., Sahin I., Gungor O., Kariper S.E., Tumer F. and Kose M., Pamoic acid esters and their xanthene derivatives: Flourimetric detection of nitroaromatic compounds and non-linear optical properties. Sensors and Actuators B: Chemical, 255 (2018) 3344-3354.
There are 19 citations in total.
Details
| Primary Language | English |
|---|---|
| Journal Section | Natural Sciences |
| Authors | |
| Publication Date | June 25, 2020 |
| Submission Date | February 2, 2020 |
| Acceptance Date | May 6, 2020 |
| Published in Issue | Year 2020Volume: 41 Issue: 2 |