CC BY-NC-ND 4.0 · Organic Materials 2021; 03(02): 303-308
DOI: 10.1055/s-0041-1729853
Emerging Stars in Organic and Polymer Materials
Short Communication

Oligofuran–Benzothiadiazole Co-oligomers: Synthesis, Optoelectronic Properties and Reactivity

a  Institute of Chemistry, The Hebrew University of Jerusalem, Edmond J. Safra Campus, Jerusalem 91904, Israel
,
b  Department of Chemical and Biomolecular Engineering, Sogang University, Seoul, 04107, South Korea
,
a  Institute of Chemistry, The Hebrew University of Jerusalem, Edmond J. Safra Campus, Jerusalem 91904, Israel
› Institutsangaben
Funding Information This work was supported by a cooperative grant from the Ministry of Science and Technology (MOST) of Israel and the Ministry of Science, ICP and Future Planning (MICP) of the Republic of Korea.


Abstract

Donor–acceptor–donor (DAD) triad systems are commonly applied as active materials in ambipolar organic field-effect transistors, organic solar cells, and NIR-emitting organic light-emitting diodes. Often, these triads utilize oligothiophenes as donors, whereas their oxygen-containing analogs, oligofurans, are far less studied in this setup. Here we introduce a family of DAD triads in which the donors are oligofurans and the acceptor is benzothiadiazole. In a combined computational and experimental study, we show that these triads display optical bandgaps similar to those of their thiophene analogs, and that a bifuran donor is sufficient to produce emission in the NIR spectral region. The presence of a central acceptor unit increases the photostability of oligofuran-based DAD systems compared with parent oligofurans of the similar length.

Supporting Information

Supporting Information for this article is available online at https://doi.org/10.1055/s-0041-1729853.


Supporting Information



Publikationsverlauf

Eingereicht: 01. Februar 2021

Angenommen: 25. März 2021

Publikationsdatum:
31. Mai 2021 (online)

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References and Notes

  • 1 Kudo K, Tanaka S, Iizuka M, Nakamura M. Thin Solid Films 2003; 438: 330
  • 2 Capelli R, Toffanin S, Generali G, Usta H, Facchetti A, Muccini M. Nat. Mater. 2010; 9: 496
  • 3 Gidron O, Varsano N, Shimon LJ. W, Leitus G, Bendikov M. Chem. Commun. 2013; 49: 6256
  • 4 Zhen S, Lu B, Xu J, Zhang S, Li Y. RSC Adv. 2014; 4: 14001
  • 5 Politis JK, Nemes JC, Curtis MD. J. Am. Chem. Soc. 2001; 123: 2537
  • 6 Gidron O, Diskin-Posner Y, Bendikov M. J. Am. Chem. Soc. 2010; 132: 2148
  • 7 Gadakh S, Shimon LJ. W, Gidron O. Angew. Chem. 2017; 129: 13789
  • 8 Glenis S, Benz M, LeGoff E, Schindler JL, Kannewurf CR, Kanatzidis MG. J. Am. Chem. Soc. 1993; 115: 12519
  • 9 Bakhshi AK, Ladik J, Seel M. Phys. Rev. B: Condens. Matter 1987; 35: 704
  • 10 González-Tejera MJ, de la Blanca ES, Carrillo I. Synth. Met. 2008; 158: 165
  • 11 Barak AH, de Ruiter G, Lahav M, Sharma S, Gidron O, Evmenenko G, Dutta P, Bendikov M, van der Boom ME. Chem. Eur. J. 2013; 19: 8821
  • 12 Gidron O, Dadvand A, Sheynin Y, Bendikov M, Perepichka DF. Chem. Commun. 2011; 47: 1976
  • 13 Shi S, Wang H, Uddin MA, Yang K, Su M, Bianchi L, Chen P, Cheng X, Guo H, Zhang S, Woo HY, Guo X. Chem. Mater. 2019; 31: 1808
  • 14 Melucci M, Favaretto L, Zanelli A, Cavallini M, Bongini A, Maccagnani P, Ostoja P, Derue G, Lazzaroni R, Barbarella G. Adv. Funct. Mater. 2010; 20: 445
  • 15 Kawabata K, Takeguchi M, Goto H. Macromol. 2013; 46: 2078
  • 16 Synthesis of DBr-1F-BT. 1F-BT (3.4 mmol, 904 mg) was dissolved in 50 mL of chloroform in a 100 mL round-bottom flask. Added some sodium bicarbonate and stirred under a CaCl2 drying tube in an ice bath. After 20 min added NBS (6.7 mmol, 1.2 g) and stirred for 1 h. The product formed as a bright orange precipitate. The solvent was evaporated almost completely, and the crude product was washed with sodium bicarbonate solution, hexane, and methanol on a sintered glass funnel to give DBr-1F-BT (1.163 g, 81%) as a bright orange solid. 1H NMR (500 MHz, chloroform-d) δ 8.00 (s, 2 H, H-C6), 7.65 (d, J = 3.5 Hz, 2 H, H-C3), 6.55 (d, J = 3.5 Hz, 2 H, H-C4) ppm. 13C NMR (126 MHz, chloroform-d) δ 152.16 (C8), 150.94 (C2), 123.53 (C6), 123.39 (C5), 121.09 (C7), 114.95 (C4), 114.52 (C3) ppm. MS (MALDI) m/z (%): 426.8565 (100, [M + H]+) calcd. for C14H6Br2O2N2S: 425.8569
  • 17 Synthesis of 2F-BT. Dry toluene (50 mL) was placed in a 250 mL oven-dried two-necked round-bottom flask and bubbled with argon while heating up to 90 °C. Added DBr-1F-BT (2.7 mmol, 1.163 g) and 2-tributylstannyl furan (5.5 mmol, 1.7 mL). Bubbled argon for 15 min, then added tetrakis(triphenylphosphine)palladium(0) (342 μmol, 395 mg), bubbled with argon for 15 more minutes, and left to stir under argon at 90 °C. After 5 h, following an evaluation of reaction progress with TLC, tetrakis(triphenylphosphine)palladium(0) (222 μmol, 257 mg) was added. The solution was bubbled with argon for 10 min and then left to stir under argon at 90 °C overnight. Next morning another TLC was done, and then the solvent was evaporated and the crude product was dissolved in DCM and filtered on celite, then washed with brine. Organic phase was dried (MgSO4) and evaporated. The resulting solid was purified by flash chromatography (SiO2, DCM:hexane 6:5) to give 2F-BT (864 mg, 79%) as a dark red solid. 1H NMR (500 MHz, Chloroform-d δ 8.12 (s, 2 H, H-C6), 7.79 (dd, J = 3.5, 0.6 Hz, 2 H, H-C5), 7.49 (dd, J = 1.8, 0.8 Hz, 2 H, H-C3), 6.80 (d, J = 3.5 Hz, 2 H, H-C4′), 6.75 (d, 2 H, H-C3′), 6.54 (dd, J = 3.4, 1.8 Hz, 2 H, H-C4) ppm. 13C NMR (126 MHz, Chloroform-d) δ 151.51 (C8), 149.55 (C5′), 146.77 (C2), 146.51 (C2′), 142.51 (C5), 123.40 (C6), 121.38 (C7), 114.50 (C4′), 111.83 (C4), 108.41 (C3′), 106.30 (C3) ppm. HR-ESI-MS m/z (%): 400.0582 (100, [M]+) calcd. for C22H12O4N2S: 400.0512
  • 18 Canola S, Mardegan L, Bergamini G, Villa M, Acocella A, Zangoli M, Ravotto L, Vinogradov SA, Di Maria F, Ceroni P, Negri F. Photochem. Photobiol. Sci. 2019; 18: 2180
  • 19 Cansu-Ergun EG, Akbayrak M, Akdag A, Önal AM. J. Electrochem. Soc. 2016; 163: G153
  • 20 Calascibetta AM, Mattiello S, Sanzone A, Facchinetti I, Sassi M, Beverina L. Molecules 2020; 25: 3717
  • 21 Jeon Y, Kim T.-M, Kim J.-J, Hong J.-I. New J. Chem. 2015; 39: 9591
  • 22 İçli-Özkut M, İpek H, Karabay B, Cihaner A, Önal AM. Polym. Chem. 2013; 4: 2457
  • 23 Mulay SV, Bogoslavky B, Galanti I, Galun E, Gidron O. J. Mater. Chem. C 2018; 6: 11951
  • 24 Yakir HR, Shimon LJ. W, Gidron O. Helv. Chim. Acta 2019; 102: e1900027