Citation: Abdullah G. Al-Sehemi, Ahmad Irfan, Abdullah M. Asiri. Red and yellow color aspects of compound 3-dicyclopropylmethylene-5-dicyanomethylene-4-diphenylmethylenetetrahydrofuran-2-one：Chromism effect[J]. Chinese Chemical Letters, ;2014, 25(4): 609-612. doi: 10.1016/j.cclet.2014.01.016 shu

Red and yellow color aspects of compound 3-dicyclopropylmethylene-5-dicyanomethylene-4-diphenylmethylenetetrahydrofuran-2-one：Chromism effect

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a Department of Chemistry, Faculty of Science, King Khalid University, Abha 61413, Saudi Arabia;
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b Unit of Science and Technology, Faculty of Science, King Khalid University, Abha 61413, Saudi Arabia;
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c Center of Excellence for Advanced Materials Research, King Khalid University, Abha 61413, Saudi Arabia;
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d Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia;
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e Center of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah 21589, Saudi Arabia

Corresponding author: Ahmad Irfan,
Received Date: 11 July 2013
Available Online: 26 November 2013

The title compound exists as yellow (1Y) and red (1R) crystals, but both gave red solutions. The intermolecular interactions between the CN parts of the crystals in 1Y are very weak. By the mechanical crushing as well as in solution 1Y again becomes red due to the absence of intermolecular interactions. We explain this color behavior by crystallochromism and solvation chromism.
- Intermolecular interactions,
- Crystallochromism,
- Solvation chromism
1. [1]
  [1] A.M.A. Asiri, H.G. Heller, M.B. Hursthouse, A. Karalulov, Tribochromic compounds, exemplified by 3-dicyclopropylmethylene-5-dicyanomethylene-4-diphenylmethylenetetrahydrofuran- 2-one, Chem. Commun. (2000) 799-800.
2. [2]
  [2] A. Irfan, R. Cui, J. Zhang, L. Hao, Push-pull effect on the charge transfer, and tuning of emitting color for disubstituted derivatives of mer-Alq3, Chem. Phys. 364 (2009) 39-45.
3. [3]
  [3] (a) A.G.Al-Sehemi, A. Irfan,A.M.Asiri,TheDFTinvestigations of the electroninjection in hydrazone-based sensitizers, Theor. Chem. Acc. 131 (2012) 1199-1208; (b) A.G. Al-Sehemi, M.A.M. Al-Melfi, A. Irfan, Electronic, optical, and charge transfer properties of donor-bridge-acceptor hydrazone sensitizers, Struct. Chem. 24 (2013) 499-506; (c) A. Irfan, A.G. Al-Sehemi, Quantum chemical study in the direction to design efficient donor-bridge-acceptor triphenylamine sensitizers with improved electron injection, J. Mol. Model. 18 (2012) 4893-4900; (d) R. Jin, A. Irfan, Theoretical study of coumarin derivatives as chemosensors for fluoride anion, Comput. Theor. Chem. 986 (2012) 93-98; (e) A. Irfan, N. Hina, A.G. Al-Sehemi, A.M. Asiri, Quantum chemical investigations aimed at modeling highly efficient zinc porphyrin dye sensitized solar cells, J. Mol. Model. 18 (2012) 4199-4207; (f) A.G. Al-Sehemi, A. Irfan, A.M. El-Agrody, Synthesis, characterization and DFT study of 4H-benzo[h]chromene derivatives, J. Mol. Struct. 1018 (2012) 171-175; (g) A. Irfan, F. Ijaz, A.G. Al-Sehemi, A.M. Asiri, Quantum chemical approach toward rational designing of highly efficient oxadiazole based oligomers used in organic field effect transistors, J. Comput. Electron 11 (2012) 374-384; (h) A.D. Becke,Density-functional thermochemistry. ⅡI.The role of exact exchange, J. Chem. Phys. 98 (1993) 5648-5652; (i) B. Miehlich, A. Savin, H. Stoll, H. Preuss, Results obtained with the correlation energy density functionals of Becke and Lee, Yang and Parr, Chem. Phys. Lett. 157 (1989) 200-206; (j) C. Lee, W. Yang, R.G. Parr, Development of the Colle-Salvetti correlationenergy formula into a functional of the electron density, Phys. Rev. B 37 (1988) 785-789.
4. [4]
  [4] M.J. Frisch, G.W. Trucks, H.B. Schlegel, et al., Gaussian 09, Revision A.1, Gaussian, Inc., Wallingford, CT, 2009.
5. [5]
  [5] A. Beck, R. Gompper, K. Polborn, H.U. Wagner, Bi[1,3-bis(dicyanomethylene)indan- 2-ylidene]-an ethylene derivative with extremely pronounced, twisting of the CC Bond, Angew. Chem. Int. Ed. Engl. 32 (1993) 1352-1354.
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