Abstract
We report nonlinear optical (NLO) investigations of few pyrazines with terminal donor groups and the influence of graphene oxide (GO) on their nonlinear absorption (NLA) under the nanosecond (ns) pulse excitation. We have used Z-scan and Degenerate Four-Wave Mixing (DFWM) techniques for the NLO investigations and a Q switched Nd:YAG laser (532 nm, 7 ns, 10 Hz) was used as the source of excitation. Modified Hummers method was used for synthesizing GO. A significant quenching in the fluorescence intensity of the pyrazine derivatives was observed when incorporating GO and it suggests the interaction between GO and pyrazine moieties through electron/energy transfer. The pyrazines/GO composites showed strong NLA and it is better than that of the parent compounds. The mechanism behind the NLA is found to be two-photon absorption (TPA) along with excited-state absorption (ESA) and the significant enhancement in the NLA activity of composites can be attributed to the photoinduced electron and/or energy transfer between the GO and pyrazine moieties.
Graphic abstract
Nonlinear optical analysis of few pyrazines with terminal donor groups and the influence of graphene oxide on their nonlinear absorption under the nanosecond pulse excitation is reported. Nonlinear absorption and optical limiting activity is found to be significantly enhanced as a result of composite formation and it is attributed to the photoinduced charge/energy transfer between two systems.
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Marder S R 2006 Organic nonlinear optical materials: where we have been and where we are going Chem. Commun. 2 131
Calvete M, Ying G and Hanack M 2004 Porphyrins and phthalocyanines as materials for optical limiting Synth. Met. 141 231
Liu Z, Zhu Y, Zhu Y, Tian J and Zheng J 2007 Study on Nonlinear Spectroscopy of Tetraphenylporphyrin and Dithiaporphyrin Diacids J. Phys. Chem. B 111 14136
Schneider A, Neis M, Stillhart M, Ruiz B, Rizwan U A K and Günter P 2006 Generation of terahertz pulses through optical rectification. in organic DAST crystals: theory and experiment Opt. Soc. Am. B 23 1822
Taniuchi T, Okada S and Nakanishi H 2004 New method to determine the refractive index and the absorption coefficient of organic nonlinear crystals in the ultra-wideband THz region Appl. Phys. Lett. 95 5984
Schulz M, Tretiak S, Chernyak Y and Mukamel S 2000 Size Scaling of Third-Order Off-Resonant Polarizabilities. Electronic Coherence in Organic Oligomers J. Am. Chem. Soc. 122 452
Wang P, Zhu P, Wu W, Kang H and Cheng Y 1999 Effect of electrolytes on the electrochemical behaviour of 11-(ferrocenylcarbonyloxy) undecanethiol SAMs on gold disk electrodes Phys. Chem. Chem. Phys. 1 3519
Benjamin J C, Fielden J, Foxon S P, Asselberghs I, Clays K and Brunschwig B S 2010 Two-Dimensional, Pyrazine-Based Nonlinear Optical Chromophores with Ruthenium(II) Ammine Electron Donors Inorg. Chem. 49 10718
Era M, Kawafuji H, Tsutsui T and Saito S 1992 Second-order nonlinear optical Langmuir-Blodgett films of pyrazine derivatives Thin Solid Films. 210/211 163
Buron F, Plé N, Turck A and Queguiner G 2005 Synthesis of Pyrazine Alcaloids from Botryllus leachi. Diazines 43 J. Org. Chem. 70 2616
Bruce A, Ellsworth Wang Y, Zhu Y, Pendri A, Gerritz S W, Sun C, et al. 2007 Synthesis and assay of isoquinoline derivatives as HIV-1 Tat–TAR interaction inhibitors Bio. Org. Med. Chem. Lett. 17 3978
Ooyama Y, Uenaka K, Harima Y and Ohshita J 2014 Development of D–π–A dyes with a pyrazine ring as an electron-withdrawing anchoring group for dye-sensitized solar cells RSC Adv. 4 30225
Wu P Z, Kim F S, Champion R D and Jenekhe S A 2008 Charge Carrier Mobility in Blends of Poly(9,9-dioctylfluorene) and Poly(3-hexylthiophene) Macromolecules 41 7021
Thomas K J R, Lin J T, Tao Y T and Chuen C H 2002 Star-Shaped Thieno-[3,4-b]-Pyrazines: A New Class of Red-Emitting Electroluminescent Materials Adv. Mater. 14 822
Lange B, Zentel R, Ober C and Marder S 2004 Photoprocessable Polymer Opals Chem. Mater. 25 5286
Zhang X L, Zhao X, Liu Z B, Liu Y S and Chen Y S 2009 Enhanced nonlinear optical properties of graphene-oligothiophene hybrid material Opt. Express 17 23959
Anand B, Kaniyoor A, Sai S S S, Philip R and Ramaprabhu S 2013 Enhanced optical limiting in functionalized hydrogen exfoliated graphene and its metal hybrids J. Mater. Chem. C 1 2773
Biswas S, Kole A K, Tiwary C S and Kumbhakar P 2016 Enhanced nonlinear optical properties of graphene oxide–silver nanocomposites measured by Z-scan technique RSC Adv. 6 10319
Zhu J, Li Y, Che Y, Wang J, Zhang B, Zhang J and Werner J B 2011 Graphene oxide covalently functionalized with zinc phthalocyanine for broadband optical limiting Carbon 49 1900
Xu Y, Liu Z, Zhang X, Wang Y, Tian J, Huang Y, Ma Y, Zhang X, Yongsheng and Chen A 2009 Graphene Hybrid Material Covalently Functionalized with Porphyrin: Synthesis and Optical Limiting Property Adv. Mater. 21 1275
Liu Z B, Zhao X and Zhang X L 2011 Ultrafast Dynamics and Nonlinear Optical Responses from sp2- and sp3-Hybridized Domains in Graphene Oxide J. Phys. Chem. Lett. 2 1972
Subrahmanyam K S, Manna A K, Pati S K and Rao C N R 2010 A study of graphene decorated with metal nanoparticles Chem. Phys. Lett. 497 70
Mamidala V, Polavarapu L, Balapanuru J, Loh K P, Xu Q and Ji W 2010 Enhanced nonlinear optical responses in donor-acceptor ionic complexes via photo induced energy transfer Opt. Express 18 25928
Xu Y, Liu Z, Zhang X, Wang Y, Tian J, Huang Y, Ma Y, Zhang X, Yongsheng and Chen A 2009 Graphene Hybrid Material Covalently Functionalized with Porphyrin: Synthesis and Optical Limiting Property Adv. Mater. 21 1275
Zhu J, Li Y and Chen Y 2011 Graphene oxide covalently functionalized with zinc phthalocyanine for broadband optical limiting Carbon 49 1900
Asiri A M, Alamry K A, Pannipara M, Al-Sehemi A G and El-Daly S A 2015 Spectroscopic investigation, photophysical parameters and DFT calculations of 4,4′-(1E,1′E)-2,2′-(pyrazine-2,5-diyl)bis(ethene-2,1-diyl)bis(N, N-dimethylaniline) (PENDA) in different solvents Spectrochim. Acta Part A 149 722
El-Daly S A, Asiri A M, Alamry K A and Osman O I 2015 Synthesis, optical properties, laser activity and DFT studies of (E, E)-2,5-bis[2-(1-methyl-1H-pyrrole-2-yl)-vinyl]pyrazine (BMPVP) J. Photochem. Photobiol. A: Chem. 312 64
El-Daly S and Alamry K A 2016 Spectroscopic Investigation and Photophysics of a D-π-A-π-D Type Styryl Pyrazine Derivative J. Fluoresc. 26 163
Hummers W S and Offeman R E 1958 Preparation of Graphitic Oxide J. Am. Chem. Soc. 80 1339
Becerril H A, Mao J, Liu Z F, Stoltenberg R M, Bao Z N and Chen Y S 2008 Evaluation of Solution-Processed Reduced Graphene Oxide Films as Transparent Conductors ACS Nano. 2 463
Sheik-Bahae M, Said A A, Wei T H, Hagan D J and van Stryland E W 1990 Sensitive Measurement of Optical Nonlinearities Using a Single Beam IEEE J. Quant. Electron. 26 760
Nasrollahzadeh M, Babaei F, Fakhri P and Jaleh B 2015 Synthesis, characterization, structural, optical properties and catalytic activity of reduced graphene oxide/copper nanocomposites RSC Adv. 5 10782
Neeta G, Chin-Pin H, Kazuhiro M, Ru-Shi L, Ram J C and Neelu C 2018 Biogenic Reduction of Graphene Oxide: An Efficient Superparamagnetic Material for Photocatalytic Hydrogen Production ACS Appl. Energy Mat. 1 5907
Zhang X F and Li F 2012 Interaction of graphene with excited and ground state rhodamine revealed by steady state and time resolved fluorescence J. Photochem. Photobiol. A: Chem. 246 8
Yang Q, Pan X J, Huang F and Li K C 2010 Fabrication of High-Concentration and Stable Aqueous Suspensions of Graphene Nanosheets by Noncovalent Functionalization with Lignin and Cellulose Derivatives J. Phys. Chem. C 114 3811
Xu Y X, Zhao L, Bai H, Hong W J, Li C and Shi G Q 2009 Chemically Converted Graphene Induced Molecular Flattening of 5,10,15,20-Tetrakis(1-methyl-4-pyridinio)porphyrin and Its Application for Optical Detection of Cadmium(II) Ions J. Am. Chem. Soc. 131 13490
Henari F Z, Blau W J, Milgrom L R, Yahioglu G, Philips D and Lacey J A 1997 Third-order optical non-linearity in Zn(II) complexes of 5,10,15,20-tetraarylethynyl-substituted porphyrins Chem. Phys. Lett. 267 229
Kiran P P, Reddy D R, Maiya B G, Dharmadhikari A K, Kumar G R and Rao D N 2005 Nonlinear absorption properties of ‘axial-bonding type’ tin(IV) tetratolylporphyrin based hybrid porphyrin arrays Opt. Commun. 252 150
Shiju E, Siji Narendran N K, Vasudevan K, Divyasree M C, Narayana Rao D and Chandrasekharan K 2017 Surface plasmon assisted enhancement in the nonlinear optical properties of phenothiazine by gold nanoparticle J. Phys. Chem. C 121 26976
He G S, Weder C, Smith P and Prasad P N 1998 Optical power limiting and stabilization based on a novel polymer compound IEEE J. Quant. Electron. 34 2279
Edappadikkunnummal S, Prasannan D, Francis J, Desai N R and Keloth C 2021 An insight into phenomenal optical non‐linearities arising from synergistic relationship between selected BODIPYs and noble metal nanoparticles Appl. Organomet. Chem. 35 e6029
Wang J, Hernandez Y and Lotya M 2009 Broadband Nonlinear Optical Response of Graphene Dispersions Adv. Mater. 21 2430
Shiju E, Siji Narendran N K, Narayana Rao D and Chandrasekharan K 2020 Enhanced nonlinear absorption and efficient power limiting action of Au/Ag@ graphite core-shell nanostructure synthesized by laser ablation Nano Express 1 030026
Qi Wang, Qin Y, Zhu Y, Huang X, Tian Y, Zhang P, et al. 2008 Optical limiting performances of multi-walled carbon nanotubols and [C60]fullerols Chem. Phys. Lett. 457 159
McLean D G, Sutherland R L, Brant M C, Brandelik D M, Fleitz P A and Pottenger T 1993 Nonlinear absorption study of a C60–toluene solution Opt. Lett. 18 858
Sreeramulu V, Haldar K K, Patra A and Narayana Rao D 2014 Nonlinear Optical Switching and Enhanced Nonlinear Optical Response of Au–CdSe Heteronanostructures J. Phys. Chem. C 118 30333
Acknowledgements
DNR acknowledges the DAE for Raja Ramanna Fellowship. DNR’s lab at the School of Physics was greatly benefitted from the interactions with Late Prof. Bhaskar G Maiya. Mehboobali Pannipara and Abdullah G-Al-Sehemi are thankful to the deanship of scientific research at King Khalid University for funding this work under the grant R.G.P.1/35/42. E. Shiju acknowledges SERB, India for providing financial assistance through NPDF (PDF/2020/002494). Deep gratitude is expressed to Prof. Chandrasekharan, NIT Calicut for the creative support.
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Shiju, E., Siji Narendran, N.K., Thomas, S. et al. Pyrazines with terminal donor groups for third-order nonlinear optics: effect of graphene oxide on nonlinear absorption. J Chem Sci 133, 95 (2021). https://doi.org/10.1007/s12039-021-01963-w
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DOI: https://doi.org/10.1007/s12039-021-01963-w