Effect of charge transfer on the first hyper-polarizability of N,N-dimethylaniline and julolidine: a DFT based comparative study.
DFT/CAM-B3LYP
First hyper-polarizability
Frequency dispersion
Hyper-Rayleigh scattering(HRS)
UV-Vis spectra
Journal
Journal of molecular modeling
ISSN: 0948-5023
Titre abrégé: J Mol Model
Pays: Germany
ID NLM: 9806569
Informations de publication
Date de publication:
27 Oct 2023
27 Oct 2023
Historique:
received:
22
05
2023
accepted:
13
10
2023
medline:
27
10
2023
pubmed:
27
10
2023
entrez:
27
10
2023
Statut:
epublish
Résumé
Quantum mechanical calculations involving electron correlation, frequency dispersion, and solvent effects were carried out to examine the second-order nonlinear optical response of various acceptor, X (-CF All computational studies have been carried out using density functional theory (DFT) based method. Since CAM-B3LYP based hybrid functional improves the asymptotic behavior of the exchange interaction by dividing into short-range and long-range components, first hyperpolarizability values in the present study were computed using DFT/ CAM-B3LYP/ 6-31G+(d,p) level of theory.
Identifiants
pubmed: 37889349
doi: 10.1007/s00894-023-05755-6
pii: 10.1007/s00894-023-05755-6
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
351Informations de copyright
© 2023. The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature.
Références
Boyd RW (1992) Nonlinear optics. Academic Press, San Diego, CA
Zyss J (ed) (1994) Molecular nonlinear optics: materials, physics and deVices. Academic Press, New York
Saleh BEA, Teich MC (1991) Fundamentals of photonics. Wiley, New York
Chemla DS, Zyss J (eds) (1987) Nonlinear optical properties of organic molecules and crystals, vol 1 and 2. Academic Press, Orlando, FL
Prasad PN, Williams D (eds) (1991) Introduction to nonlinear effects in molecules and polymers. J. Wiley, New York
Nalwa HS, Miyata S (eds) (1997) Nonlinear optics of organic molecules and polymers. CRC Press, Boca Raton, FL
Kanis DR, Ratner MA, Marks TJ (1994) Design and construction of molecular assemblies with large second-order optical nonlinearities. Quantum Chemical Aspects. Chem Rev 94:195–242
Zyss J, Ledoux I (1994) nonlinear optics in multipolar media: theory and experiments. Chem Rev 94:77–105
Torre G, Vázquez P, Agullo-Lopez F, Torres T (2004) Role of structural factors in the nonlinear optical properties of phthalocyanines and related compounds. Chem Rev 104:3723–3750
pubmed: 15352778
Ostroverkhova O, Moerner WE (2004) Organic photorefractives: mechanisms, materials, and applications. Chem Rev 104:3267–3314
pubmed: 15250742
Burland DM, Miller RD, Walsh CA (1994) Second-order nonlinearity in poled-polymer systems. Chem Rev 94:31–75
Eisenthal KB (2006) Second harmonic spectroscopy of aqueous nano- and microparticle interfaces. Chem Rev 106:1462–1477
pubmed: 16608187
Papadopoulos MG, Leszczynski J, Sadlej AJ (2006) Nonlinear optical properties of matter: from molecules to condensed phases. Kluwer, Dordrecht
Asselberghs I, Clays K, Persoons A, Ward MD, McCleverty JA (2004) Switching of molecular second-order polarisability in solution. J Mater Chem 14:2831–2839
Coe BJ (2006) Switchable nonlinear optical metallochromophores with pyridinium electron acceptor groups. Acc Chem Res 39:383–393
pubmed: 16784216
Dalton LR, Sullivan PA, Bale DH (2010) Electric field poled organic electro-optic materials: state of the art and future prospects. Chem Rev 110:25–55
pubmed: 19848381
Radhakrishnan TP (2008) Molecular structure, symmetry, and shape as design elements in the fabrication of molecular crystals for second harmonic generation and the role of molecules-in-materials. Acc Chem Res 41:367–376
pubmed: 18260652
Willets KA, Nishimura SY, Schuck PJ, Twieg RJ, Moerner WE (2005) Nonlinear optical chromophores as nanoscale emitters for single-molecule spectroscopy. Acc Chem Res 38:549–556
pubmed: 16028889
Dalton LR (2007) In: Skotheim TA, Reynolds JR (eds) Handbook of conducting polymers. CRC Press LLC, Boca Raton, FL
Bhatacharyya AK, Nandi DK (1976) Synthesis of N,N-dimethylaniline from aniline and methanolin. Eng Chem Prod Res Dev 15(3):201–206
Mandal U, Samanta SS, Beg H, Misra A (2023) Investigation of first hyper-polarisability molecular switches between enol–keto equilibrium of phenyl benzodifurantrione: a DFT-based computational study. Mol Phys 121(3):e2161964
Enami Y, Derose CT, Mathine D, Loychik C, Greenlee C, Norwood RA, Kim TD, Luo J, Tian Y, Jen AKY, Peyghambarian N (2007) Hybrid polymer/sol-gel waveguide modulations with exceptionally large electro-optic coefficients. Nat Photonics 1:423–423
Shi YQ, Zhang C, Zhang H, Bechtel JH, Dalton LR, Robinson BH, Steier WH (2000) Low (sub-1-volt) halfwave voltage polymeric electro-optic modulators achieved by controlling chromophore shape. Science 288:119–122
pubmed: 10753112
Datta A, Pal S (2005) Effects of conjugation length and donor–acceptor functionalization on the non-linear optical properties of organic push–pull molecules using density functional theory. J Mol Struct THEOCHEM 715:59–64
Garza AJ, Osman OI, Wazzan NA, Khan SB, Asiri AM, Scuseria GE (2014) A Computational study of the nonlinear optical properties of carbazole derivatives: theory refines experiment. Theor Chem Acc 133:1458
Siddiqui SA, Rasheed T, Faisal M, Pandey AK, Khan SB (2012) Electronic structure, nonlinear optical properties, and vibrational analysis of gemifloxacin by density functional theory. Spectroscopy 27:185–206
Janjua MRSA, Amin M, Ali M, Bashir B, Khan MU, Iqbal MA, Guan W, Yan L, Su Z-M (2012) A DFT study on the two-dimensional second-order nonlinear optical (NLO) Response of terpyridine-substituted hexamolybdates: physical insight on 2D inorganic–organic hybrid functional materials. Eur J Inorg Chem 2012:705–711
Janjua MRSA, Khan MU, Bashir B, Iqbal MA, Song Y, Naqvi SAR, Khan ZA (2012) Effect of π-conjugation spacer (CC) on the first hyperpolarizabilities of polymeric chain containing polyoxometalate cluster as a side-chain pendant: a DFT study. Theor Chem 994:34–40
Marder SR, Cheng LT, Tiemann BG, Friedli AC, Blancharddesce M, Perry JW, Skindhoj J (1994) Large 1st hyperpolarizabilities in push-pull polyenes by tuning of the bond-length alternation and aromaticity. Science 263:511–514
pubmed: 17754885
Cleuvenbergen SV, Asselberghs I, Vanormelingen W, Verbiest T, Franz E, Clays K, Kuzyk MG, Koeckelberghs G (2014) Record-high hyperpolarizabilities in conjugated polymers. J Mater Chem C 2:4533–4538
Luo J, Lin F, Li ZA, Li M, Kim TD, Jang SH, Jen AKY (2017) New push-pull polyene chromophores containing a Michler’s base donor and a tricyanofuran acceptor: multicomponent condensation, allopolar isomerism and large optical nonlinearity. J Mater Chem C 2(5):2230–2234
Wu J, Liu J, Zhou T, Bo S, Qiu L, Zhen Z, Liu X (2012) Enhanced electro-optic coefficient (r33) in nonlinear optical chromospheres with novel donor structure. RSC Adv 2:1416
Wu J, Bo S, Liu J, Zhou T, Xiao H, Qiu L, Zhen Z, Liu X (2012) Synthesis of novel nonlinear optical chromophore to achieve ultrahigh electro-optic activity. Chem Commun 48:9637–9639
Hu CL, Chen Z, Xiao HY, Zhen Z, Liu XH, Bo SH (2017) Synthesis and characterization of a novel indoline based nonlinear optical chromophore with excellent electro-optic activity and high thermal stability by modifying the pi-conjugated bridges. J Mater Chem C 5:5111–5118
Islam MM, Bhuiyan MDH, Bredow T, Try A (2011) Theoretical investigation of the nonlinear optical properties of substituted anilines and N, N-dimethylanilines. Comput Theor Chem 967:165–170
Borbulevych OY, Clark RD, Romero A, Tan L, Antipin MY, Nesterov VN, Cardelino BH, Moore CE, Sanghadasa M, Timofeeva TV (2002) Experimental and theoretical study of the structure of N,N-dimethyl-4-nitroaniline derivatives as model compounds for non-linear optical organic materials. J Mol Struct 604:73–86
Malina I, Kampars V, Turovska B, Belyakov S (2017) Novel green-yellow-orange-red light emitting donor-π-acceptor type dyes based on 1,3-indandione and dimedone moieties. Dyes Pigments 139:820–830
Liu F, Fan C, Tu Y, Pu S (2018) A new fluorescent and colorimetric chemosensor for Al3+ and F-/CN- based on a julolidine unit and its bioimaging in living cells. RSC Adv 8(54):31113–31120
pubmed: 35548728
pmcid: 9085603
Varejão JOS, Varejão EVV, Fernandes SA (2019) Synthesis and derivatization of julolidine: a powerful heterocyclic structure. Eur J Org Chem 2019:4273–4310
Xu L, Li X, Zhu Y, Xiang Y (2009) One-pot synthesis of N,N-dimethylaniline from nitrobenzene and methanol. New J Chem 33:2051–2054
Galus Z, Adams RN (1962) Anodic oxidation studies of N,N-dimethylaniline. II. Stationary and rotated disk studies at inert electrodes. J Am Chem Soc 84(11):2061–2065
Bersohn R, Pao YH, Frisch HL (1966) Double-quantum light scattering by molecules. J Chem Phys 45:3184
Kleinman DA (1962) Nonlinear dielectric polarization in optical media. Phys Rev 126:1977
Guillaume M, Champagne B, Markova N, Enchevand V, Castet F (2007) Ab initio investigation on the second-order nonlinear optical responses in keto− enol equilibria of salicylideneanilines. J Phys Chem A 111(39):9914
Brasselet S, Zyss J (1998) Multipolar molecules and multipolar fields: probing and controlling the tensorial nature of nonlinear molecular media. J Opt Soc Am B 15:257
Rodriguez V, Grondin J, Adamietz F, Danten Y (2010) Local structure in ionic liquids investigated by hyper-Rayleigh scattering. J Phys Chem B 114:15057
pubmed: 21028886
Tomasi J and Persico M. (1994) Molecular interactions in solution: an overview of methods based on continuous distributions of the solvent. Chem. Rev. 94:2027 (b) Tomasi J, Mennucci B and Cammi R. (2005) Quantum mechanical continuum solvation models. Chem. Rev. 105:2999
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson, GA, Nakatsuji H-Li-X,Caricato M, Marenich AV, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, 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 Jr. JA, Peralta JE, Ogliaro F, Bearpark MJ, Heyd JJ, Brothers EN, Kudin KN, Staroverov VN, Keith TA, Kobayashi R, Normand J, Raghavachari K, Rendell AP, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB, Fox DJ. (2016) Gaussian, Inc., Gaussian 16, Revision B.01 (Wallingford CT GaussView 5.0. Wallingford, E.U.A.).
Rankine CD, Nunes JPF, Feixas TWBL, Young S, Wann DA (2018) Structure of 4-(dimethylamino)benzonitrile using gas electron diffraction : a new lease of life for the only gas electron diffractometer in the UK. J Phys Chem A 122(25):5656–5665
pubmed: 29870255
Nouar SL (2021) Solvent effect on hyper-Rayleigh scattering (HRS) first hyperpolarizability of substituted polyene: part (I). J Fundam Appl Sci 13:1175–1192
Castet F, Bogdan E, Plaquet A, Ducasse L, Champagne B, Rodriguez V (2012) Reference molecules for nonlinear optics: a joint experimental and theoretical investigation. J Chem Phys 136:024506
pubmed: 22260602
Gheribi R, Hadji D, Ghallab R, Medjani M, Benslimane M, Trifa C, Dénès G, Merazig H (2022) Synthesis, spectroscopic characterization, crystal structure, Hirshfeld surface analysis, linear and NLO properties of new hybrid compound based on tin fluoride oxalate and organic amine molecule (C12N2H9)2[SnF2(C2O4)2]2H2O. J Mol Struct 1248:131392
Hadji D (2021) Phosphates branching effect on the structure, linear and NLO properties of linear phosphazenes. Mater Chem Phys 262:124280
Kenane A, Hadji D, Argoub K et al (2023) Efficient NLO materials based on poly(ortho-anisidine) and polyaniline: a quantum chemical study. J Electron Mater 52:530–539
Bensafi T, Hadji D, Yahiaoui A, Argoub K, Hachemaoui A, Kenane A, Baroudi B, Toubal K, Djafri A, Benkouider AM (2021) Synthesis, characterization and DFT calculations of linear and NLO properties of novel (Z)-5-benzylidene-3-N(4-methylphenyl)-2-thioxothiazolidin-4-one. J Sulfur Chem 42(6):645–663
Hadji D, Brahim H (2018) Structural, optical and nonlinear optical properties and TD-DFT analysis of heteroleptic bis-cyclometalated iridium (III) complex containing 2-phenylpyridine and picolinate ligands. Theor Chem Acc 137:180
Bhattacharyya K, Chowdhury M (1993) Environmental and magnetic field effects on exciplex and twisted charge transfer emission. Chem Rev 93(1):507–535
Guan W, Liu CG, Song P et al (2009) Quantum chemical study of redox-switchable second-order optical nonlinearity in Keggin-type organoimido derivative [PW11O39(ReNC
Oudar JL, Chemla DS (1977) Hyperpolarizabilities of the nitroanilines and their relations to the excited state dipole moment. J Chem Phys 66:2664–2668
Zhang X, Wu H-Q, Xu H-L, Sun S-L, Su Z-M (2015) Modulating the charge transfer of D–S–A molecules: structures and NLO properties. J Phys Chem A 119:767–773
pubmed: 25535806