Exploration of optoelectronic, nonlinear and charge transport properties of hydroquinoline derivatives by DFT approach

• Autorzy: Irfan Ahmad , Al-Sehemi Abdullah G. , Chaudhry Aijaz Rasool , Muhammad Shabbir , Jin Ruifa

Identyfikatory

DOI

10.2478/msp-2020-0041

• Języki publikacji: EN

Abstrakty

EN

Present investigation deals with an in depth study of three compounds including 4-(4-chlorophenyl)-8-methyl-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile (1), 4-(4-bromophenyl)-8-methyl-2-oxo-1,2,3,4,4a,5,6,7-octahydroquinoline-3-carbonitrile (2) and 8-methyl-2-oxo-4-(thiophen-2-yl)-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile (3) with respect to their structural, electronic, optical and charge transport properties. The ground and excited states geometries were optimized by density functional theory (DFT) and time dependent DFT, respectively. To rationalize the adopted methodology, the calculated geometrical parameters at ground state were compared with the experimental crystal structures. Several quantum chemical insights including the analysis of frontier molecular orbitals (FMOs), total/partial density of states (T/PDOS), molecular electrostatic potentials (MEP), local and global reactivity descriptors revealed that the studied compounds would be efficient multifunctional materials. The absorption wavelengths as well as their major transitions were thoroughly studied at TD-B3LYP/6-31G** level of theory. The smaller hole reorganization energies indicate that all these compounds might show better hole transport tendency. The anionic geometry relaxation of compound 2 is larger than the cationic form which leads to higher electron reorganization energy revealing the reduction of electron charge transport as compared to the hole.

Słowa kluczowe

EN

hydroquinoline; electro-optical properties; charge transport properties; reorganization energy; nonlinear optical properties

• Wydawca: De Gruyter
• Czasopismo: Materials Science Poland
• Rocznik: 2020
• Tom: Vol. 38, No. 2
• Strony: 284--295
• Opis fizyczny: Bibliogr. 71 poz., tab., rys.

Twórcy

autor

Irfan Ahmad

• Department of Chemistry, Faculty of Science, King Khalid University, Abha 61413, P.O. Box 9004, Saudi Arabia
• Research Center for Advanced Materials Science (RCAMS), King Khalid University, Abha 61413, P.O. Box 9004, Saudi Arabia

autor

Al-Sehemi Abdullah G.

• Department of Chemistry, Faculty of Science, King Khalid University, Abha 61413, P.O. Box 9004, Saudi Arabia

autor

Chaudhry Aijaz Rasool

• Deanship of Scientific Research, University of Bisha, Bisha 61922, PO Box 199, Saudi Arabia

autor

Muhammad Shabbir

• Department of Physics, Faculty of Science, King Khalid University, Abha 61413, P.O. Box 9004, Saudi Arabia

autor

Jin Ruifa

• College of Chemistry and Chemical Engineering, Chifeng University, Chifeng, China

Bibliografia

• [1] MASSARANI E., NARDI D., POZZI R., DEGEN L., MAGISTRETTI M.J., J. Med. Chem., 13 (1970), 380.
• [2] SEGAL I., ZABLOTSKAYA A., LUKEVICS E., Chem. Heterocycl. Compd., 41 (2005), 613.
• [3] ABDEL-GAWAD S.M., EL-GABY M.S.A., HEIBA H.I., ALY H.M., GHORAB M.M., J. Chin. Chem. Soc., 52 (2005), 1227.
• [4] LEVINE H., 3RD, DING Q., WALKER J.A., VOSS R.S., AUGELLI-SZAFRAN C.E., Neurosci. Lett., 465 (2009), 99.
• [5] ADHIKARI A., KALLURAYA B., SUJITH K.V., GOUTHAMCHANDRA, MAHMOOD R., Saudi Pharmaceutical J., 20 (2012), 75.
• [6] HUIGUO LAI G.S.P., RADHAKRISHNAN PADMANABHAN, Antiviral Res., 97 (2013), 74.
• [7] IRFAN A., CUI R., ZHANG J., Chem. Phys., 358 (2009), 25.
• [8] IRFAN A., CUI R., ZHANG J., NADEEM M., Aust. J. Chem., 63 (2010), 1283.
• [9] PRACHAYASITTIKUL V P.S., RUCHIRAWAT S, PRACHAYASITTIKUL V, Drug Des. Dev. Ther., 7 (2013), 1157.
• [10] CHUPAKHINA T.A., KATSEV A.M., KUR’YANOV V.O., USS. J. Bioorg. Chem., 38 (2012), 422.
• [11] BEN KHALIFA M., VAUFREY D., TARDY J., Org. Electron., 5 (2004), 187.
• [12] LENZI O., COLOTTA V., CATARZI D., VARANO F., SQUARCIALUPI L., FILACCHIONI G., VARANI K., VINCENZI F., BOREA P.A., BEN D.D., LAMBERTUCCI C., CRISTALLI G., Biorg. Med. Chem., 19 (2011), 3757.
• [13] SHEN A.-Y., WU S.-N., CHIU C.-T., J. Pharm. Pharmacol., 51 (1999), 543.
• [14] BAHGAT K., RAGHEB A.G., Central European J. Chem., 5 (2007), 201.
• [15] TENG Y.H.K., SU Z.M., LIAO Y., YANG S.Y., WANG R.S., Theor. Chem. Acc., 117 (2007), 1.
• [16] RAMS-BARON M.D., MROZEK-WILCZKIEWICZ A., KORZEC M., CIESLIK W., SPACZY´NSKA E., BARTCZAK P., RATUSZNA A., POLANSKI J., MUSIOL R., PLoS One, 10 (2015), e0131210.
• [17] ASIRI A.M., AL-YOUBI A.O., FAIDALLAH H.M.,BADAHDAH K.O., NG S.W., Acta Crystallogr. Sect. E,67 (2011), o2596.
• [18] ASIRI A.M., FAIDALLAH H.M., NG S.W., TIEKINKE.R.T., Acta Crystallogr. Sect. E, 68 (2012), o2376.
• [19] ASIRI A.M., FAIDALLAH H.M., SAQER A.A.A., NG S.W., TIEKINK E.R.T., Acta Crystallogr. Sect. E, 68 (2012), o2291.
• [20] LI Y., ZOU L.-Y., REN A.-M., FENG J.-K., Comp.Theor. Chem., 981 (2012), 14.
• [21] CHAUDHRY A.R., AHMED R., IRFAN A., MUHAMMAD S., SHAARI A., AL-SEHEMI A.G., Comp. Theor. Chem., 1045 (2014), 123.
• [22] IRFAN A., AL-SEHEMI A.G., AL-ASSIRI M.S., Comp. Theor. Chem., 1031 (2014), 76.
• [23] ZGIERSKI M.Z., LIM E.C., FUJIWARA T., Comp. Theor. Chem., 1036 (2014), 1.
• [24] MAHMOOD A., TAHIR M.H., IRFAN A., AL-SEHEMI A.G., AL-ASSIRI M., Comp. Theor. Chem., 1066 (2015), 94.
• [25] IRFAN A., ABDULLAH G., ABDULLAH M.A., J. Theor. Comput. Chem., 11 (2012), 631.
• [26] IRFAN A., J. Theor. Comput. Chem., 13 (2014), 1450013.
• [27] A. IRFAN S., MUHAMMAD, A.G. AL-SEHEMI, M.S. AL-ASSIRI, A. KALAM, A.R. CHAUDHRY, J Theor Comput Chem, 14 (2015), 1550027.
• [28] MUHAMMAD S., IRFAN A., AL-SEHEMI A.G., ALASSIRI M.S., KALAM A., CHAUDHRY A.R., J. Theor. Comput. Chem., 14 (2015), 1550029.
• [29] BECKE A.D., J. Chem. Phys., 98 (1993), 5648.
• [30] SALVATORI P., AMAT A., PASTORE M., VITILLARO G., SUDHAKAR K., GIRIBABU L., SOUJANYA Y., ANGELIS DE F., Comp. Theor. Chem., 1030 (2014), 59.
• [31] FU J.-J., DUAN Y.-A., ZHANG J.-Z., GUO M.-S., LIAO Y., Comp. Theor. Chem., 1045 (2014), 145.
• [32] IRFAN A., KALAM A., CHAUDHRY A.R., AL-SEHEMI A.G., MUHAMMAD S., Optik - Intern. J. Light Elect. Optics, 132 (2017), 101.
• [33] SÁNCHEZ-CARRERA R.S., COROPCEANU V., SILVA DA FILHO D.A., FRIEDLEIN R., OSIKOWICZ W., MURDEY R., SUESS C., SALANECK W.R., BRÉDAS J.-L., J. Phys. Chem. B, 110 (2006), 18904.
• [34] WONG B.M., CORDARO J.G., J. Chem. Phys., 129 (2008).
• [35] MATCZAK P., Comp. Theor. Chem., 983 (2012), 25.
• [36] FEREYDUNI E., VESSALLY E., YAAGHUBI E., SUNDARAGANESAN N., Spectrochimica Acta A, 81 (2011), 64.
• [37] IRFAN A., AL-SEHEMI A.G., CHAUDHRY A.R.,
• [38] STRASSNER T., TAIGE M.A., J. chem. theor. comput., 1 (2005), 848.
• [39] SOUSA S.F., FERNANDES P.A., RAMOS M.J., J. Phys. Chem. A, 111 (2007), 10439.
• [40] MUSA K.A.K., ERIKSSON L.A., J. Phys. Chem. A, 112(2008), 10921.
• [41] GUILLAUMONT D., NAKAMURA S., Dyes Pigm., 46 (2000), 85.
• [42] AL-SEHEMI A., AL-MELFI M., IRFAN A., Struct. Chem., 24 (2013), 499.
• [43] IRFAN A., AL-SEHEMI A., J. Mol. Model., 18 (2012), 4893.
• [44] IRFAN A., HINA N., AL-SEHEMI A., ASIRI A., J. Mol. Model., 18 (2012), 4199.
• [45] IRFAN A., AL-SEHEMI A.G., KALAM A., J. Mol. Struct., 1049 (2013), 198.
• [46] AL-SEHEMI A.G., IRFAN A., AL-MELFI M.A.M., Spectrochim. Acta A, 145 (2015), 40.
• [47] IRFAN A., JIN R., AL-SEHEMI A.G., ASIRI A.M., Spectrochim. Acta A, 110 (2013), 60.
• [48] AL-SEHEMI A.G., IRFAN A., FOUDA A.M., Spectrochim. Acta A, 111 (2013), 223.
• [49] TRUJILLO C., LAMSABHI A.M., MÓ O., YÁÑEZ M., SALPIN J.-Y., Int. J. Mass Spectrom., 306 (2011), 27.
• [50] BEGTRUP M., BALLE T., CLARAMUNT R.M.A., SANZ D., JIMÉNEZ J.A., MÓ O., YÁÑEZ M., ELGUERO J., J. Mol. Struct. (TheoChem), 453 (1998), 255.
• [51] CORRAL I., MÓ O., YÁÑEZ M., Int. J. Mass spectrom., 255 – 256 (2006), 20.
• [52] ZHANG C., LIANG W., CHEN H., CHEN Y., WEI Z., WU Y., J. Mol. Struct. (TheoChem), 862 (2008), 98.
• [53] IRFAN A., AL-SEHEMI A.G., MUHAMMAD S., CHAUDHRY A.R., KALAM A., SHKIR M., ALSALAMI A.E., ASIRI A.M., J. Saudi. Chem. Soc., 20 (2016), 680.
• [54] IRFAN A., AL-SEHEMI A.G., MUHAMMAD S., CHAUDHRY A.R., AL-ASSIRI M.S., JIN R., KALAM A., SHKIR M., ASIRI A.M., Comptes Rendus Chim., 18 (2015), 1289.
• [55] SCALMANI G., FRISCH M.J., MENNUCCI B., TOMASI J., CAMMI R., BARONE V., J. Chem. Phys., 124 (2006), 094107.
• [56] MARCUS R.A., Rev. Mod. Phys., 65 (1993), 599.
• [57] BRÉDAS J.L., CALBERT J.P., DA SILVA FILHO D.A., CORNIL J., Proc. Natl. Acad. Sci., 99 (2002), 5804.
• [58] GRUHN N.E., DA SILVA FILHO D.A., BILL T.G., MALAGOLI M., COROPCEANU V., KAHN A., BRÉDAS J.-L., J. Am. Chem. Soc., 124 (2002), 7918.
• [59] REIMERS J.R., J. Chem. Phys., 115 (2001), 9103.
• [60] M. J. FRISCH G.W.T., SCHLEGEL H.B., SCUSERIA G.E., ROBB M.A., CHEESEMAN J.R., SCALMANI G., BARONE V., MENNUCCI B., PETERSSON G.A., NAKATSUJI H., CARICATO M., LI X., HRATCHIAN H.P., IZMAYLOV A.F., BLOINO J., ZHENG G., SONNENBERG J.L., HADA M., EHARA M., TOYOTA K., FUKUDA R., HASEGAWA J., ISHIDA M., NAKAJIMA T., HONDA Y., KITAO O., NAKAI H., VREVEN T., MONTGOMERY J.A. JR., PERALTA J.E., OGLIARO F., BEARPARK M., HEYD J.J., BROTHERS E., KUDIN K.N., STAROVEROV V.N., KOBAYASHI R., NORMAND J., RAGHAVACHARI K., RENDELL A., BURANT J.C., IYENGAR S.S., TOMASI J., COSSI M., REGA N., MILLAM J.M., KLENE M., KNOX J.E., CROSS J.B., BAKKEN V., ADAMO C., JARAMILLO J., GOMPERTS R., STRATMANN R.E., YAZYEV O., AUSTIN A.J., CAMMI R., POMELLI C., OCHTERSKI J.W., MARTIN R.L., MOROKUMA K., ZAKRZEWSKI V.G., VOTH G.A., SALVADOR P., DANNENBERG J.J., DAPPRICH S., DANIELS A.D., FARKAS Ö., FORESMAN J.B., ORTIZ J.V., CIOSLOWSKI J., FOX D.J., in: Gaussian 09, Revision A. 01„ Gaussian Inc., Wallingford, CT, 2009.
• [61] CLARK S.J., SEGALL M.D., PICKARD C.J., HASNIP P.J., PROBERT M.I., REFSON K., PAYNE M.C., Z. Kristallogr. Cryst. Mater., 220 (2005), 567.
• [62] MATERIALSSTUDIO, (2013).
• [63] PERDEW J.P., WANG Y., Phys. Rev. B, 45 (1992), 13244.
• [64] AYERS P.W., PARR R.G., J. Am. Chem. Soc., 122 (2000), 2010.
• [65] MORELL C., GRAND A., TORO-LABBÉ A., J. Phys.Chem. A, 109 (2005), 205.
• [66] LEVINE B.F., BETHEA C.G., J. Chem. Phys., 63 (1975), 2666.
• [67] BADAN J., HIERLE R., PERIGAUD A., ZYSS J., WILLIAMS D., NLO properties of organic molecules and polymeric materials, in: American Chemical Society Symposium Series, American Chemical Society Washington DC, 1993.
• [68] MUHAMMAD S., IRFAN A., SHKIR M., CHAUDHRY A.R., KALAM A., ALFAIFY S., AL-SEHEMI A.G., AL-SALAMI A., YAHIA I., XU H.L., J. Comput. Chem., 36 (2015), 118.
• [69] KURTZ H.A., STEWART J.J.P., DIETER K.M., J. Comput. Chem., 11 (1990), 82.
• [70] NAGAPANDISELVI P., BABY C., GOPALAKRISHNAN R., J. Mol. Struct., 1056 – 1057 (2014), 110.
• [71] DEHU C., MEYERS F., BREDAS J.L., J. Am. Chem. Soc., 115 (1993), 6198.