Download PDF
CC BY-NC-ND 4.0 · Organic Materials 2023; 5(01): 35-47
DOI: 10.1055/a-1972-5895
Original Article

Broadly Applicable Synthesis of Heteroarylated Dithieno[3,2-b:2′,3′-d]pyrroles for Advanced Organic Materials – Part 1: Conducting Electropolymers

Christoph Lorenz
a   Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany
,
Astrid Vogt
a   Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany
,
Judith Millan 
b   Dpto. de Química – Facultad de Ciencia y Tecnología, Universidad de la Rioja, Madre de Dios, 53, 26006 Logroño-La Rioja, España
,
Elena Mena-Osteritz 
a   Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany
,
Peter Bäuerle 
a   Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany
› Author Affiliations
› Further Information
   Permissions and Reprints All articles of this category


Abstract

Herein, a novel and versatile method for the synthesis of N-heteroarylated dithieno[3,2-b:2,3′-d]pyrroles (DTPs) is reported. By microwave-assisted Cu-catalyzed coupling of parent H-DTP 1 with 5- and 6-membered heteroaromatic halides, a variety of novel N-functionalized DTPs were obtained. Supported by quantum chemical calculations and X-ray structure analysis, structural and optoelectronic properties of the π-conjugated systems were investigated and led to valuable structure–property relationships. Selected derivatives were electropolymerized to corresponding conducting DTP polymers.

Key words

organic materials - conjugated molecules - dithienopyrrole - Cu-catalyzed C – N coupling - optoelectronic properties - quantum chemical calculations - electropolymerization - poly(dithienopyrrole)

Supporting Information



Publication History

Received: 12 August 2022

Accepted after revision: 27 October 2022

Accepted Manuscript online:
04 November 2022

Article published online:
27 January 2023

© 2023. The authors. 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

  • 1 Zhang X, Steckler TT, Dasari RR, Ohira S, Potscavage Jr WJ, Prakash Tiwari S, Coppée S, Ellinger S, Barlow S, Brédas J-L, Kippelen B, Reynolds JR, Marder SR. J. Mater. Chem. 2010; 20: 123
    CrossrefPubMed
  • 2 Lu H-I, Lu C-W, Lee Y-C, Lin H-W, Lin L-Y, Lin F, Chang J-H, Wu C-I, Wong K-T. Chem. Mater. 2014; 26: 4361
    CrossrefPubMed
  • 4 Rasmussen SC, Uzelac EJ, Culver EW. Adv. Heterocycl. Chem. 2020; 10: 75
    CrossrefPubMed
  • 5 Förtsch S. PhD thesis. University of Ulm; 2018
    PubMedGoogle Scholar
  • 6 Gronowitz S. Thiophene and its derivatives.. Weissberger A, Taylor EC. The Chemistry of Heterocyclic Hompounds. 44.2. J. Wiley & Sons; New York: 1986: 631
    Google Scholar
  • 7 Förtsch S, Vogt A, Bäuerle P. J. Phys. Org. Chem. 2017; 30: e3743
    CrossrefPubMed
  • 8 Yin X, Zhou J, Song Z, Dong Z, Bao Q, Shrestha N, Bista SS, Ellington RJ, Yan Y, Tang W. Adv. Funct. Mater. 2019; 29: 1904300
    CrossrefPubMed
  • 9 Cao J, Du F, Yang L, Tang W. J. Mater. Chem. A 2020; 8: 22572
    CrossrefPubMed
  • 10 Vogt A, Schwer F, Förtsch S, Lorenz C, Mena-Osteritz E, Aubele A, Kraus T, Bäuerle P. Chem. Eur. J. 2021; 27: 12362
    CrossrefPubMed
  • 11 Kwon JK, Cho JH, Ryu Y-S, Oh SH, Yum EK. Tetrahedron 2011; 67: 4820
    CrossrefPubMed
  • 12 Wetzel C, Brier E, Vogt A, Mishra A, Mena-Osteritz E, Bäuerle P. Angew. Chem. Int. Ed. 2015; 54: 12334
    CrossrefPubMed
  • 13 Evenson SJ, Pappenfus TM, Ruiz Delgado MC, Radke-Wohlers KR, López-Navarrete JT, Rasmussen SC. Phys. Chem. Chem. Phys. 2012; 14: 6101
    CrossrefPubMed
  • 14 Ates M, Arican F, Karazehir T. Bull. Mater. Sci. 2013; 36: 1281
    CrossrefPubMed
  • 15 Förtsch S, Bäuerle P. Polym. Chem. 2017; 8: 3586
    CrossrefPubMed
  • 16 Audebert P, Miomandre F. Skotheim TA, Reynolds JR. Electrochemistry of Conducting Polymers in Handbook of Conducting Polymers. 3rd ed. CRC Press; Boca Raton, USA: 2007: 1
    Crossref
  • 17 Förtsch S, Mena-Osteritz E, Bäuerle P. Polym. Chem. 2021; 12: 3332
    CrossrefPubMed
  • 18 Volkov AV, Wijeratne K, Mitraka E, Ail U, Zhao D, Tybrandt K, Andreasen JW, Berggren M, Crispin X, Zozulenko IV. Adv. Funct. Mater. 2017; 27: 1700329
    CrossrefPubMed
  • 19 Araujo RB, Banerjee A, Panigrahi P, Yang L, Sjödin M, Strømme M, Araujo CM, Ahuja R. Phys. Chem. Chem. Phys. 2017; 19: 3307
    CrossrefPubMed
  • 20 Almalki M, Lorenz C, Vogt A, Alanazi A, Gao J, Zakeeruddin SM, Bäuerle P, Eickemeyer FT, Grätzel M. Org. Mater. 2023; 5: 48
    Article in Thieme ConnectPubMed
  • 21 CryaAlisPro, Agilent Technologies XRD Products
    PubMed
  • 22 Palatinus L, Chapuis G. J. Appl. Crystallogr. 2007; 40: 786
    CrossrefPubMed
  • 23 Palatinus L, van der Lee A. J. Appl. Crystallogr. 2008; 41: 975
    CrossrefPubMed
  • 24 Palatinus L, Prathapa SJ, van Smaalen S. J. Appl. Crystallogr. 2012; 45: 575
    CrossrefPubMed
  • 25 Sheldrick GM. Acta Crystallogr. Sect. A: Found. 2008; 64: 112
    CrossrefPubMed
  • 26 Frisch MJ. Gaussian, Inc.. Wallingford, CT: 2013
    PubMed
  • 27 Melas-Kyriazi J, Ding IK, Marchioro A, Punzi A, Hardin BE, Burkhard GF, Tétreault N, Grätzel M, Moser J-E, McGehee MD. Adv. Energy Mater. 2011; 1: 407
    CrossrefPubMed
  • 28 Wang Y-K, Yuan Z-C, Shi G-Z, Li Y-X, Li Q, Hui F, Sun B-Q, Jiang Z-Q, Liao L-S. Adv. Funct. Mater. 2016; 26: 1375
    CrossrefPubMed
  • 29 Kim G-W, Choi H, Kim M, Lee J, Son SY, Park T. Adv. Energy Mater. 2020; 10: 1903403
    CrossrefPubMed
  • 30 Pham HD, Yang TC-j, Jain SM, Wilson GJ, Sonar P. Adv. Energy Mater. 2020; 10: 1903326
    CrossrefPubMed