Abstract
Organic semiconductors with extended π-conjugate systems have been extensively investigated to be implemented and improve optoelectronic devices. It is well known that benzothiadiazole (BTD) derivatives have interesting semiconductor properties that make them suitable materials for optoelectronic applications. In this work, the photophysical properties of 4 BTD with triphenylmethyl and triphenylsilyl derivatives in solution exhibited larger Stokes shifts, which can be attributed to the length and conjugation of these molecules. On the other hand, the quantum yields observed for these systems were larger than 0.5. In addition, the formation of Langmuir monolayers at the air–water interface with isotherms showing high collapse pressures around 60 mN/m, and stable compression–decompression cycles (hysteresis) were obtained. Langmuir–Blodgett films onto glass substrates were formed with these compounds by using the Z-type deposit with transfer ratios close to 1. In addition, high-fluorescence emission responses were observed for the BTD derivatives that did not contain silicon in their structure. Also, using scanning electron and atomic force microscopies, regular surface morphologies were observed for the silicon-less compounds, but higher roughnesses and fiber-like structures for the other films. From these results, these BTD films can be potential candidates to be employed in photoelectronic applications.
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Agina EV, Mannanov AA, Sizov AS, Vechter O, Borshchev OV, Bakirov AV, Shcherbina MA, Chvalun SN, Konstantinov VG, Bruevich VV, Kozlov OV, Pshenichnikov MS, Paraschuk DY, Ponomarenko SA (2017) Luminescent organic semiconducting Langmuir monolayers. ACS Appl Mater Interfaces 9:18078–18086. https://doi.org/10.1021/acsami.7b01919
Araujo FT, Peres LO, Caseli L (2019) Conjugated polymers blended with lipids and galactosidase as Langmuir-Blodgett films to control the biosensing properties of nanostructured surfaces. Langmuir 35:7294–7303. https://doi.org/10.1021/acs.langmuir.9b00536
Azarova NA, Owen JW, McLellan CA, Grimminger MA, Chapman EK, Anthony JE, Jurchescu OD (2010) Fabrication of organic thin film transistors by spray-deposition for low-cost, large-area electronics. Org Electron 11:1960–1965. https://doi.org/10.1016/j.orgel.2010.09.008
Bai H, Wang Y, Cheng P, Li Y, Zhu D, Zhan X (2014) Acceptor-donor-acceptor small molecules based on indacenodithiophene for efficient organic solar cells. ACS Appl Mater Interfaces 6:8426–8433. https://doi.org/10.1021/am501316y
Bulumulla C, Gunawardhana R, Kularatne RN, Hill ME, McCandless GT, Biewer MC, Stefan MC (2018) Thieno[3,2- b] pyrrole-benzothiadiazole banana-shaped small molecules for organic field-effect transistors. ACS Appl Mater Interfaces 10:11818–11825. https://doi.org/10.1021/acsami.8b01113
De Barros A, Constantino CJL, Bortoleto JRR, Da Cruz NC, Ferreira M (2016) Incorporation of gold nanoparticles into Langmuir-Blodgett films of polyaniline and montmorillonite for enhanced detection of metallic ions. Sens Actuat B Chem 236:408–417. https://doi.org/10.1016/j.snb.2016.06.022
Dey B, Debnath P, Chakraborty S, Deb B, Bhattacharjee D, Majumdar S, Hussain SA (2017) Study of compression-induced supramolecular nanostructures of an imidazole derivative by Langmuir-Blodgett technique. Langmuir 33:8383–8394. https://doi.org/10.1021/acs.langmuir.7b01750
Dou L, You J, Hong Z, Xu Z, Li G, Street RA, Yang Y (2013) 25th anniversary article: a decade of organic/polymeric photovoltaic research. Adv Mater 25:6642–6671
He Y, Wang R, Jiao T, Yan X, Wang M, Zhang L, Bai Z, Zhang Q, Peng Q (2019) Facile preparation of self-assembled layered double hydroxide-based composite dye films as new chemical gas sensors. ACS Sustain Chem Eng 7:10888–10899. https://doi.org/10.1021/acssuschemeng.9b01780
He Y, Wang R, Sun C, Liu S, Zhou J, Zhang L, Jiao T, Peng Q (2020) Facile synthesis of self-assembled NiFe layered double hydroxide-based azobenzene composite films with photoisomerization and chemical gas sensor performances. ACS Omega 5:3689–3698. https://doi.org/10.1021/acsomega.9b04290
Hu W (2013) Organic optoelectronics. Wiley-VCH, Weinheim
Jiménez-Urias A, Lugo-Aranda AZ, Miranda-Olvera M, Farfán N, Santillan R, Arcos-Ramos R, Carreón-Castro MP (2018) Synthesis and characterization of dumbbell-like BTD-based derivatives to engineer organic building blocks in solid-state. J Mol Struct 1153:34–41. https://doi.org/10.1016/j.molstruc.2017.09.106
Kim H, Reddy MR, Kim H, Choi D, Kim C, Seo SY (2017a) Benzothiadiazole-based small-molecule semiconductors for organic thin film transistors and complementary-like inverters. Chem Plus Chem 82:742–749. https://doi.org/10.1002/cplu.201700070
Kim K, Inagaki Y, Kanehashi S, Ogino K (2017b) Incorporation of benzothiadiazole moiety at junction of polyfluorene–polytriarylamine block copolymer for effective color tuning in organic light emitting diode. J Appl Polym Sci. https://doi.org/10.1002/app.45393
Lee CW, Kim OY, Lee JY (2014) Organic materials for organic electronic devices. J Ind Eng Chem 20:1198–1208. https://doi.org/10.1016/j.jiec.2013.09.036
Li M, An C, Pisula W, Müllen K (2018) Cyclopentadithiophene-benzothiadiazole donor-acceptor polymers as prototypical semiconductors for high-performance field-effect transistors. Acc Chem Res 51:1196–1205. https://doi.org/10.1021/acs.accounts.8b00025
Martín R, Prieto P, Carrillo JR, Rodríguez AM, De Cozar A, Boj PG, Díaz-García MA, Ramírez MG (2019) Design, synthesis and amplified spontaneous emission of 1,2,5-benzothiadiazole derivatives. J Mater Chem C 7:9996–10007. https://doi.org/10.1039/c9tc03148k
Olla T, Ibraikulov OA, Ferry S, Boyron O, Méry S, Heinrich B, Heiser T, Léveque P, Leclerc N (2019) Benzothiadiazole halogenation impact in conjugated polymers, a comprehensive study. Macromolecules 52:8006–8016. https://doi.org/10.1021/acs.macromol.9b01760
Ostroverkhova O (2016) Organic optoelectronic materials: mechanisms and applications. Chem Rev 116:13279–13412
Patel HA, Bhanvadia VJ, Mande HM, Zade SS, Patel AL (2019) Benzochalcogendiazole-based conjugated molecules: investigating the effects of substituents and heteroatom juggling. Org Biomol Chem 17:9467–9478. https://doi.org/10.1039/c9ob01762c
Patterson M, Vogel HJ, Prenner EJ (2017) The effect of repeated lateral compression and expansions mimicking blinking on selected tear film polar lipid monofilms. Biochim Biophys Acta 1859:319–330. https://doi.org/10.1016/j.bbamem.2016.12.010
Pazini A, Maqueira L, Avila HC, Valente FM, Aderne RE, Back D, Aucélio RQ, Cremona M, Limberger J (2018) Phenoxy-benzothiadiazole dyes: synthesis, photophysical properties and preliminary application in OLEDs. Tetrahedron Lett 59:2994–2999. https://doi.org/10.1016/j.tetlet.2018.06.052
Petty MC (1996) Langmuir-blodgett films: an introduction. Cambridge University Press, Cambridge
Revoju S, Biswas S, Eliasson B, Sharma GD (2019) Phenothiazine-based small molecules for bulk heterojunction organic solar cells; variation of side-chain polarity and length of conjugated system. Org Electron 65:232–242. https://doi.org/10.1016/j.orgel.2018.11.024
Riera-Galindo S, Tamayo A, Mas-Torrent M (2018) Role of polymorphism and thin film morphology in organic semiconductors processed by solution shearing. ACS Omega 3:2329–2339. https://doi.org/10.1021/acsomega.8b00043
Rodríguez-Seco C, Biswas S, Sharma GD, Vidal-Ferran A, Palomares E (2018) Benzothiadiazole substituted semiconductor molecules for organic solar cells: the effect of the solvent annealing over the thin film hole mobility values. J Phys Chem C 122:13782–13789. https://doi.org/10.1021/acs.jpcc.8b00840
Seck M, Vincze A, Satka A, Hasko D, Uherek F, Tournebize A, Peisert H, Chasse T (2015) Characterization of the degradation process of Si-PCPDTBT:PC70BM(1:2) blend layers deposited on ITO/glass substrate. Sol Energy Mater Sol Cells 132:210–214. https://doi.org/10.1016/j.solmat.2014.09.014
Tsegaye AA, Waryo TT, Baker PG, Iwuoha EI (2016) Electropolymerization and spectroelectrochemical properties of poly(4,7-dithien-2-yl-2,1,3-benzothiadiazole) films in three 1-butyl-3-methylimidazolium ionic liquids. Mater Chem Phys 171:57–62. https://doi.org/10.1016/j.matchemphys.2015.10.059
Wang J, Yan H, Liu Z, Wang Z, Gao H, Zhang Z, Wang B, Xu N, Zhang S, Liu X, Zhang R, Wang X, Zhang G, Zhao L, Liu K, Sun X (2018) Langmuir-Blodgett self-assembly of ultrathin graphene quantum dot films with modulated optical properties. Nanoscale 10:19612–19620. https://doi.org/10.1039/c8nr05159c
Whiteside PJD, Chininis JA, Hunt HK (2016) Techniques and challenges for characterizing metal thin films with applications in photonics. Coatings. https://doi.org/10.3390/coatings6030035
Yao Y, Dong H, Hu W (2016) Charge transport in organic and polymeric semiconductors for flexible and stretchable devices. Adv Mater 28:4513–4523. https://doi.org/10.1002/adma.201503007
Zaumseil J, Sirringhaus H (2007) Electron and ambipolar transport in organic field-effect transistors. Chem Rev 107:1296–1323. https://doi.org/10.1021/cr0501543
Zhang J, Xu W, Sheng P, Zhao G, Zhu D (2017) Organic donor-acceptor complexes as novel organic semiconductors. Acc Chem Res 50:1654–1662. https://doi.org/10.1021/acs.accounts.7b00124
Acknowledgements
MDP Carreón-Castro acknowledges to DGAPA-UNAM for financial support (PAPIIT IN-206018). V. Alvarez-Venicio acknowledges to CONACyT for the cathedra 411-2016. E. de la O-Cuevas acknowledges to CONACyT for scholarship 619615. M. Rivera acknowledges DGAPA-UNAM grant PAPIIT- IN-112420. The authors would like to express their gratitude to Alejandra Ortega and Martín Cruz Villafañe (ICN-UNAM), Manuel Aguilar Franco, Jaqueline R. D. Cañetas Ortega, Diego Quiterio Vargas (IF-UNAM), for technical assistance and LUCE-ICAT-UNAM.
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Álvarez-Venicio, V., Caldera-Villalobos, M., Arcos-Ramos, R. et al. Photophysical and morphological properties of Langmuir–Blodgett films of benzothiadiazole derivatives. Chem. Pap. 75, 967–978 (2021). https://doi.org/10.1007/s11696-020-01366-0
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DOI: https://doi.org/10.1007/s11696-020-01366-0