CC BY-NC-ND 4.0 · Organic Materials 2021; 03(02): 321-336
DOI: 10.1055/s-0041-1730934
Focus Issue: Supramolecular Optoelectronic Materials
Short Review

Supramolecular Thiophene-Based Materials: A Few Examples of the Interplay between Synthesis, Optoelectronic Properties and Applications

a  ISOF, CNR Area della Ricerca di Bologna, Via P. Gobetti 101, 40129 Bologna, Italy
,
a  ISOF, CNR Area della Ricerca di Bologna, Via P. Gobetti 101, 40129 Bologna, Italy
,
a  ISOF, CNR Area della Ricerca di Bologna, Via P. Gobetti 101, 40129 Bologna, Italy
› Institutsangaben


Abstract

Supramolecular nanostructured thiophene based materials with optoelectronic functions are of wide current interest and are playing a crucial role in different fields of nanoscience and nanotechnology. This short review gives a concise report of some particularly interesting examples from our own work concerning thiophene-based supramolecular architectures at multiple length scales, their function and application in devices. We start with some general considerations on the great chemical diversity of thiophene derivatives and their supramolecular architectures. Then we focus on how the supramolecular organization of specific thiophene derivatives may generate nanostructures that enable new functions and applications in devices. For each example, we report the synthesis of the corresponding thiophene derivatives.

1. Introduction

2. Supramolecular Organization may Impart New Functions to the System

3. Supramolecular and Optoelectronic Properties of Oligothiophene-S,S-dioxides

4. Colloidal Nanoparticles formed by Self-Assembly of Thiophene-Based Polymers

5. Conclusions and Outlook



Publikationsverlauf

Eingereicht: 22. März 2021

Angenommen: 21. April 2021

Publikationsdatum:
18. Juni 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

    • 1a Archna; Pathania S, Chawla PA. Bioorg. Chem. 2020; 101: 104026
    • 1b Shah R, Verma PK. Chem. Cent. J. 2018; 12: 137
    • 1c Singh A, Singh G, Singh Bedi PM. J. Heterocycl. Chem. 2020; 57: 2658
    • 1d Apetrei RM, Camurlu P. J. Electrochem. Soc. 2020; 167: 037557
    • 1e Bhilare NV, Auti PB, Marulkar VS, Pise VJ. Mini-Rev. Med. Chem. 2021; 21: 217
    • 1f Amna B, Siddiqi HM, Hassana A, Ozturk T. RSC Adv. 2020; 10: 4322
    • 1g Li L, Zhao C, Wang H. Chem. Rec. 2016; 16: 797
    • 1h Qiao Y, Yin X, Tang C. Sci. China Chem. 2015; 58: 1641
    • 1i Perepichka IF, Perepichka DF. Handbook of Thiophene-Based Materials: Applications in Organic Electronics and Photonics. Wiley; Chichester: 2009
    • 1j Rasmussen SC, Evenson SJ, McCausland CB. Chem. Commun. 2015; 51: 4528
    • 1k Barbarella G, Zangoli M, Di Maria F. Adv. Heterocycl. Chem. 2017; 123: 105
    • 1l Zangoli M, Di Maria F, Barbarella G. ChemistryOpen 2020; 9: 499
  • 2 Barbarella G, Zambianchi M, Bongini A, Antolini L. Adv. Mater. 1993; 5: 384
  • 3 Bongini A, Bottoni A. J. Phys. Chem. A 1999; 103: 6800
  • 4 Loi MA, Da Como E, Dinelli F, Murgia M, Zamboni R, Biscarini F, Muccini M. Nat. Mater. 2005; 4: 81
  • 5 Melucci M, Barbarella G, Zambianchi M, Di Pietro P, Bongini A. J. Org. Chem. 2004; 69: 4821
  • 6 Melucci M, Gazzano M, Barbarella G, Cavallini M, Biscarini F, Maccagnani P, Ostoja P. J. Am. Chem. Soc. 2003; 125: 10266
  • 7 Milanese E, Brink T, Aghababaei R, Molinari JF. Nat. Commun. 2019; 10: 1116
  • 8 Palamà IE, Di Maria F, D'Amone S, Barbarella G, Gigli G. J. Mater. Chem. B 2015; 3: 151
    • 9a Palamà I, Di Maria F, Viola I, Fabiano E, Gigli G, Bettini C, Barbarella G. J. Am. Chem. Soc. 2011; 133: 17777
    • 9b Viola I, Palamà IE, Coluccia AM. L, Biasiucci M, Dozza B, Lucarelli E, Di Maria F, Barbarella G, Gigli G. Integr. Biol. 2013; 5: 1057
    • 9c Moros M, Di Maria F, Dardano P, Tommasini G, Castillo-Michel H, Kovtun A, Zangoli M, Blasio M, De Stefano L, Tino A, Barbarella G, Tortiglione C. iScience 2020; 23: 101022
  • 10 Chernyatina AA, Nicolet S, Aebi U, Herrmann H. Proc. Natl. Acad. Sci. U.S.A. 2012; 109: 13620
  • 11 Melucci M, Barbarella G, Sotgiu G. J. Org. Chem. 2002; 67: 8877
    • 12a Alesi S, Di Maria F, Melucci M, Macquarrie DJ, Luque R, Barbarella G. Green Chem. 2008; 10: 517
    • 12b Di Maria F, Barbarella G. J. Sulfur Chem. 2013; 34: 627
  • 13 Mazzeo M, Vitale V, Della Sala F, Anni M, Barbarella G, Favaretto L, Sotgiu G, Cingolani R, Gigli G. Adv. Mater. 2005; 17: 34
    • 14a Helten H. Chem. Asian J. 2019; 14: 919
    • 14b Yin X, Liu J, Jäkle F. Chem. Eur. J. 2021; 27: 2973
    • 15a Li B, Li Z, Guo F, Song J, Jiang X, Wang Y, Gao S, Wang J, Pang X, Zhao L, Zhang Y. ACS Appl. Mater. Interfaces 2020; 12: 14233
    • 15b Li D, Hu W, Wang J, Zhang Q, Cao XM, Ma X, Tian H. Chem. Sci. 2018; 9: 5709
  • 16 Cicoira F, Santato C, Melucci M, Favaretto L, Gazzano M, Muccini M, Barbarella G. Adv. Mater. 2006; 18: 169
  • 17 Chaudhry MU, Muhieddine K, Wawrzinek R, Sobus J, Tandy K, Lo SC, Namdas EB. Adv. Funct. Mater. 2020; 30: 1905282
  • 18 Viola I, Mazzeo M, Passabì A, D'Amone S, Cingolani R, Gigli G. Adv. Mater. 2005; 17: 2935
    • 19a Viola I, Della Sala F, Piacenza M, Favaretto L, Gazzano M, Anni M, Barbarella G, Cingolani R, Gigli G. Adv. Mater. 2007; 19: 1597
    • 19b Viola I, Piliego C, Favaretto L, Barbarella G, Cingolani R, Gigli G. ACS Appl. Mater. Interfaces 2010; 2: 484
    • 20a Pisignano D, Anni M, Gigli G, Cingolani R, Zavelani-Rossi M, Lanzani G, Barbarella G, Favaretto L. Appl. Phys. Lett. 2002; 81: 3534
    • 20b Pisignano D, Mele E, Persano L, Gigli G, Visconti P, Cingolani R, Barbarella G, Favaretto L. Phys. Rev. B: Condens. Matter 2004; 70: 205206
  • 21 Ghofraniha N, Viola I, Di Maria F, Barbarella G, Gigli G, Conti C. Laser Photonics Rev. 2013; 7: 432
  • 22 Sapienza R. Nat. Rev. Phys. 2019; 1: 690
    • 23a Barbarella G, Favaretto L, Sotgiu G, Zambianchi M, Antolini L, Pudova O, Bongini A. J. Org. Chem. 1998; 63: 5497
    • 23b Di Maria F, Zangoli M, Palamà IE, Fabiano E, Zanelli A, Monari M, Perinot A, Caironi M, Maiorano V, Maggiore A, Pugliese M, Salatelli E, Gigli G, Viola I, Barbarella G. Adv. Funct. Mater. 2016; 26: 6970
  • 24 Rozen S, Bareket Y. J. Org. Chem. 1997; 62: 1457
    • 25a Barbarella G, Favaretto L, Zambianchi M, Pudova O, Arbizzani C, Bongini A, Mastragostino M. Adv. Mater. 1998; 10: 551
    • 25b Wei S, Xia J, Dell EJ, Jiang Y, Song R, Lee H, Rodenbough P, Briseno AL, Campos LM. Angew. Chem. 2014; 126: 1863
  • 26 Barbarella G, Favaretto L, Sotgiu G, Zambianchi M, Bongini A, Arbizzani C, Mastragostino M, Anni M, Gigli G, Cingolani R. J. Am. Chem. Soc. 2000; 122: 11971
  • 27 Li J, Wang J, Li H, Song N, Wang D, Tang BZ. Chem. Soc. Rev. 2020; 49: 1144
  • 28 Antolini L, Tedesco E, Barbarella G, Favaretto L, Sotgiu G, Zambianchi M, Casarini D, Gigli G, Cingolani R. J. Am. Chem. Soc. 2000; 122: 9006
  • 29 Anni M, Della Sala F, Raganato MF, Fabiano E, Lattante S, Cingolani R, Gigli G, Barbarella G, Favaretto L, Görling A. J. Phys. Chem. B 2005; 109: 6004
  • 30 Giglia G, Inganäs O, Anni M, De Vittorio M, Cingolani R, Barbarella G, Favaretto L. Appl. Phys. Lett. 2001; 78: 1493
    • 31a Mariano F, Mazzeo M, Duan Y, Barbarella G, Favaretto L, Carallo S, Cingolani R, Gigli G. Appl. Phys. Lett. 2009; 94: 063510
    • 31b Gigli G, Anni M, Theander M, Cingolani R, Barbarella G. Synth. Met. 2001; 119: 581
  • 32 Walzer K, Maennig B, Pfeiffer M, Leo K. Chem. Rev. 2007; 107: 1233
    • 33a Dell EJ, Capozzi B, Xia J, Venkataraman L, Campos LM. Nat. Chem. 2015; 7: 209
    • 33b Busby E, Xia J, Low JZ, Wu Q, Hoy J, Campos LM, Sfeir MY. J. Phys. Chem. B 2015; 119: 7644
    • 34a Wang Y, Feng L, Wang S. Adv. Funct. Mater. 2019; 29: 1806818
    • 34b MacFarlane LR, Shaikh H, Garcia-Hernandez JD, Vespa M, Fukui T, Manners I. Nat. Rev. Mater. 2021; 6: 7
    • 34c Zangoli M, Di Maria F. View 2020; 2: 20200086
    • 34d Monti F, Manfredi G, Palamà IE, Kovtun A, Zangoli M, D'Amone S, Ortolani L, Bondelli G, Szreder T, Bobrowski K, D'Angelantonio M, Lanzani G, Di Maria F. Adv. Healthcare Mater. 2021; 10: 2001306
    • 34e Di Maria F, Lodola F, Zucchetti E, Benfenati F, Lanzani G. Chem. Soc. Rev. 2018; 47: 4757
    • 34f Zangoli M, Di Maria F, Zucchetti E, Bossio C, Antognazza MR, Lanzani G, Mazzaro R, Corticelli F, Baroncini M, Barbarella G. Nanoscale 2017; 9: 9202
    • 34g Palamà IE, Di Maria F, Zangoli M, D'Amone S, Manfredi G, Barsotti J, Lanzani G, Ortolani L, Salatelli E, Gigli G, Barbarella G. RSC Adv. 2019; 9: 23036
    • 35a Maya-Vetencourt JF, Manfredi G, Mete M, Colombo E, Bramini M, Di Marco S, Shmal D, Mantero G, Dipalo M, Rocchi A, DiFrancesco ML, Papaleo ED, Russo A, Barsotti J, Eleftheriou C, Di Maria F, Cossu V, Piazza F, Emionite L, Ticconi F, Marini C, Sambuceti G, Pertile G, Lanzani G, Benfenati F. Nat. Nanotechnol. 2020; 15: 698
    • 35b Tortiglione C, Antognazza MR, Tino A, Bossio C, Marchesano V, Bauduin A, Zangoli M, Morata SV, Lanzani G. Sci. Adv. 2017; 3: e1601699
    • 35c Bossio C, Aziz IA, Tullii G, Zucchetti E, Debellis D, Zangoli M, Di Maria F, Lanzani G, Antognazza MR. Front. Bioeng. Biotechnol. 2018; 6: 1
  • 36 Millstone JE, Kavulak DF. J, Woo CH, Holcombe TW, Westling EJ, Briseno AL, Toney MF, Fréchet JM. J. Langmuir 2010; 26: 13056
  • 37 Di Maria F, Zanelli A, Liscio A, Kovtun A, Salatelli E, Mazzaro R, Morandi V, Bergamini G, Shaffer A, Rozen S. ACS Nano 2017; 11: 1991
    • 38a Shimizu H, Yamada M, Wada R, Okabe M. Polym. J. 2008; 40: 33
    • 38b Rao JP, Geckeler KE. Prog. Polym. Sci. 2011; 36: 887
  • 39 Melitz W, Shen J, Kummel AC, Lee S. Surf. Sci. Rep. 2011; 66: 1
  • 40 Li X, Perera K, He J, Gumyusenge A, Mei J. J. Mater. Chem. C 2019; 7: 12761
  • 41 Österholm AM, Shen DE, Gottfried DS, Reynolds JR. Adv. Mater. Technol. 2016; 1: 1600063
  • 43 Moreira T, Laia CA. T, Zangoli M, Antunes M, Di Maria F, De Monte S, Liscio F, Parola AJ, Barbarella G. ACS Appl. Polym. Mater. 2020; 2: 3301
  • 44 Zucchetti E, Zangoli M, Bargigia I, Bossio C, Di Maria F, Barbarella G, D'Andrea C, Lanzani G, Antognazza MR. J. Mater. Chem. B 2017; 5: 565
  • 45 Barbarella G, Bongini A, Zambianchi M. Macromolecules 1994; 27: 3039
  • 46 Lehn JM. Angew. Chem. Int. Ed. 2015; 54: 3276
    • 47a Di Maria F, Zangoli M, Gazzano M, Fabiano E, Gentili D, Zanelli A, Fermi A, Bergamini G, Bonifazi D, Perinot A, Caironi M, Mazzaro R, Morandi V, Gigli G, Liscio A, Barbarella G. Adv. Funct. Mater. 2018; 28: 1801946
    • 47b Zangoli M, Gazzano M, Monti F, Maini L, Gentili D, Liscio A, Zanelli A, Salatelli E, Gigli G, Baroncini M, Di Maria F. ACS Appl. Mater. Interfaces 2019; 11: 16864
    • 47c Di Maria F, Fabiano E, Gentili D, Biasiucci M, Salzillo T, Bergamini G, Gazzano M, Zanelli A, Brillante A, Cavallini M, Della Sala F, Gigli G, Barbarella G. Adv. Funct. Mater. 2014; 24: 4943