A novel optical power-limiter-stabilizer candidate: Two-photon active chromophores derived from thiazolothiazole

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Published: Mar 4, 2024
DOI: https://doi.org/10.14456/apst.2024.34
Keywords:
Two-photon absorption Two-photon-induced fluorescence Optical power-limiting Thiazolothiazole

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Rizki R. Saputra
Faculty of Mathematics and Natural Sciences, University of Palangka Raya, Palangka Raya, Indonesia
Novia E. Setyatama
College of Sciences, National Central University, Taoyuan, Taiwan
Muhammad D. Ramadhan
Clean Energy Research Center, Korea Institute of Science and Technology, Seoul, South Korea
Mahathir M. E. Raharjo
Faculty of Mathematics and Natural Sciences, University of Brawijaya, Malang, Indonesia
Jeddah Yanti
Faculty of Mathematics and Natural Sciences, Universitas Negeri Makassar, Makassar, Indonesia
Dianisa K. Sandi
Faculty of Mathematics and Natural Sciences, Universitas Sebelas Maret, Surakarta, Indonesia

Abstract

Thiazolo[5,4-d]thiazole (TTz) was exploited as the electron-acceptor, diphenylamine as the electron-donor, and fluorene/fluorene-thiophene as the electron-bridge to create two new donor-acceptor-donor (D-A-D) type chromophores, 2DFL-TTz and 2DFL-Th-TTz. The structural characteristics of the chromophores were determined using UV spectroscopy, 1H and 13C NMR, and mass spectroscopic methods. Their linear and nonlinear optical properties were determined using Fluoromax. The outcomes showed that under femtosecond laser irradiation at 800 nm, the 2DFL-Th-TTZ compound displayed robust two-photon induced fluorescence. The two-photon excited fluorescence (2PEF) technique was employed to map the two-photon absorption spectra of 2DFL-Th-TTZ. The findings showed that this chromophore displayed strong two-photon activity (>500 GM) in the 680-850 nm spectral range, making it a possible candidate for an optical power limiter or optical power stabilizer.


 

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How to Cite
Saputra, R. R., Setyatama, N. E., Ramadhan, M. D., Raharjo, M. M. E., Yanti, J. ., & Sandi, D. K. (2024). A novel optical power-limiter-stabilizer candidate: Two-photon active chromophores derived from thiazolothiazole. Asia-Pacific Journal of Science and Technology, 29(02), APST–29. https://doi.org/10.14456/apst.2024.34
Issue
Vol. 29 No. 02 (2024): MAR-APR
Section
Research Articles
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This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

References

Yılmaz H, Küçüköz B, Sevinç G, Tekin S, Yaglioglu HG, Hayvalı M, et al. The effect of charge transfer on the ultrafast and two-photon absorption properties of newly synthesized boron-dipyrromethene compounds. Dyes Pigments. 2013;99(3):979-985.

Lemercier G, Four M, Chevreux S. Two-photon absorption properties of 1,10-phenanthroline-based Ru(II) complexes and related functionalized nanoparticles for potential application in two-photon excitation photodynamic therapy and optical power limiting. Coordin Chem Rev. 2018;368:1-12.

Wang G, Bennett D, Zhang C, Coileáin C, Liang M, McEvoy N, et al. Two-photon absorption in monolayer MXenes. Adv Opt Mater. 2020;8(9):1902021.

Sayresmith NA, Saminathan A, Sailer JK, Patberg SM, Sandor K, Krishnan Y, et al. Photostable voltage-sensitive dyes based on simple, solvatofluorochromic, asymmetric thiazolothiazoles. J Am Chem Soc. 2019;141(47):18780-18790.

Rajashekar B, Sowmendran P, Sai SSS, Rao GN. Synthesis, characterization and two-photon absorption based broadband optical limiting in diarylideneacetone derivative. J Photoch Photobio A. 2012;238:20-23.

Tang C, Zheng Q, Zhu H, Wang L, Chen SC, Ma E, et al. Two-photon absorption and optical power limiting properties of ladder-type tetraphenylene cored chromophores with different terminal groups. J Mater Chem C. 2013;1(9):1771-1780.

Li Y, Zheng M, Wang J, Gao Y, Zhang B, Yang W. Two-photon absorption and fluorescence fluoride-sensing properties of N-octyl-3,6-bis[4-(4-(diphenylamino)phenyl)phenyl]-1,4-diketo-pyrrolo[3,4-c]pyrrole. Dyes Pigments. 2014;104:97-101.

Torres TC, López PN, Gutiérrez MH, Valdez TM, López OJ, Terrones M. Optoelectronic modulation by multi-wall carbon nanotubes. Nanotechnology. 2013;24(4):045201.

Gandra N, Chiu PL, Li W, Anderson YR, Mitra S, He H, et al. Photosensitized singlet oxygen production upon two-photon excitation of single-walled carbon nanotubes and their functionalized analogues. J Phy Chem C. 2009;113(13):5182-5185.

Rahulan KM, Flower NAL, Sujatha RA, Padmanathan N, Gopalakrishnan C. Nonlinear optical absorption studies of CoMoO4 hybrid nanostructures. J Mater Sci Mater Electron. 2018;29(2):1504-1549.

Zheng XL, Yang L, Shang B, Wang MQ, Niu Y, Li WQ, et al. Two-dimensional two-photon absorptions and third-order nonlinear optical properties of Ih fullerenes and fullerene onions. Phys Chem Chem Phys. 2020;22(25):14225-14235.

Yang CC, Duan X, Li L, Zheng XL, Chen J, Tian WQ, et al. BN-doped carbon nanotubes and nanoribbons as nonlinear-optical functional materials for application in second-order nonlinear optics. ACS Appl Nano Mater. 2023;6(3):1549-1561.

Wang ZM, Neogi A. Nanoscale photonics and optoelectronics. 1st ed. New York: Springer; 2010.

Chen Y, Du Z, Chen W, Wen S, Sun L, Liu Q, et al. New small molecules with thiazolothiazole and benzothiadiazole acceptors for solution-processed organic solar cells. New J Chem. 2014;38(4):1559-1564.

Jung JY, Han SJ, Chun J, Lee C, Yoon J. New thiazolothiazole derivatives as fluorescent chemosensors for Cr3+ and Al3+. Dyes Pigments. 2012;94(3):423-426.

Kumar V, Sony S, Kaur N, Mobin SM, Kaur P, Singh K. Thiazolothiazole based donor-π-acceptor fluorophore: Protonation/deprotonation triggered molecular switch, sensing and bio-imaging applications. Anal Chim Acta. 2022;1206:339776.

Lim DH, Jang SY, Kang M, Lee S, Kim YA, Heo YJ, et al. A systematic study on molecular planarity and D–A conformation in thiazolothiazole- and thienylenevinylene-based copolymers for organic field-effect transistors. J Mater Chem C. 2017;5(39):10126-10132.

Nazim M, Ameen S, Akhtar MS, Lee YS, Shin HS. Novel thiazolothiazole based linear chromophore for small molecule organic solar cells. Chem Phys Lett. 2013;574:89-93.

Cheng P, Shi Q, Lin Y, Li Y, Zhan X. Evolved structure of thiazolothiazole based small molecules towards enhanced efficiency in organic solar cells. Org Electron. 2013;14(2):599-606.

Amna B, Siddiqi HM, Hassan A, Ozturk T. Recent developments in the synthesis of regioregular thiophene-based conjugated polymers for electronic and optoelectronic applications using nickel and palladium-based catalytic systems. RSC Adv. 2020;10(8):4322-4396.

Zhang HC, Guo EQ, Zhang YL, Ren PH, Yang WJ. Donor-acceptor-substituted anthracene-centered cruciforms: synthesis, enhanced two-photon absorptions, and spatially separated frontier molecular orbitals. Chem Mater. 2009;21(21):5125-5135.

Lin TC, Chen YF, Hu CL, Hsu CS. Two-photon absorption and optical power limiting properties in femtosecond regime of novel multi-branched chromophores based on tri-substituted olefinic scaffolds. J Mater Chem. 2009;19(38):7075-7080.

Kannan R, He GS, Lin TC, Prasad PN, Vaia RA, Tan LS. Toward highly active two-photon absorbing liquids. synthesis and characterization of 1,3,5-triazine-based octupolar molecules. Chem Mater. 2004;16(1):185-194.

Zhu X, Tian C, Jin T, Wang J, Mahurin SM, Mei W, et al. Thiazolothiazole-linked porous organic polymers. Chem Commun. 2014;50(95):15055-15058.

Pavia DL, Lampman GM, Kriz GS, Vyvyan JR. Introduction to spectroscopy. 5th ed. Massachusetts: Cengage Learning; 2015.

Zhou H, Zheng Z, Xu G, Yu Z, Yang X, Cheng L, et al. 1, 3, 5-triazine-cored derivatives dyes containing triphenylamine based two-photon absorption: synthesis, optical characterization and bioimaging. Dyes Pigm. 2012;94(3):570-582.

Shao J, Guan Z, Yan Y, Jiao C, Xu QH, Chi C. Synthesis and characterizations of star-shaped octupolar triazatruxenes-based two-photon absorption chromophores. J Org Chem. 2011;76(3):780-790.

Zhang D, Gao Y, Dong J, Sun Q, Liu W, Xue S, et al. Two-photon absorption and piezofluorochromism of aggregation-enhanced emission 2,6-bis(p-dibutylaminostyryl)-9,10-bis(4-pyridylvinyl-2) anthracene. Dyes Pigm. 2015;113:307-311.