Synlett 2020; 31(06): 632-634
DOI: 10.1055/s-0039-1690828
cluster
© Georg Thieme Verlag Stuttgart · New York

1,2,4-Triphenylpyrroles: Synthesis, Structure and Luminescence Properties

Joana R. M. Ferreira
a   QOPNA, LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal   Email: sguieu@ua.pt
,
Raquel Nunes da Silva 
a   QOPNA, LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal   Email: sguieu@ua.pt
b   Institute of Biomedicine (iBiMED), Department of Medical Sciences, University of Aveiro, 3810-193 Aveiro, Portugal
,
João Rocha
c   CICECO, Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
,
Artur M. S. Silva 
a   QOPNA, LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal   Email: sguieu@ua.pt
,
Samuel Guieu∗
a   QOPNA, LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal   Email: sguieu@ua.pt
c   CICECO, Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
› Author AffiliationsThanks are due to the University of Aveiro, FCT/MEC for financial support to the QOPNA research Unit (FCT UID/QUI/00062/2019), CICECO–Aveiro Institute of Materials (FCT Ref. UID/CTM/50011/2019), financed by national funds through FCT/MEC, and also to the Portuguese NMR Network. This work was also supported by the Integrated Programme of SR&TD ‘pAGE – Protein Aggregation Across the Lifespan’ (reference CENTRO-01-0145-FEDER-000003), co-funded by the Centro 2020 program, Portugal 2020, and the European Union, through the European Regional Development Fund.
Further Information

Publication History

Received: 07 January 2020

Accepted after revision: 31 January 2020

Publication Date:
13 February 2020 (online)

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Abstract

Pyrroles are widely found in natural products and play an important role in biological processes. Certain pyrrole derivatives are fluorescent and may be used as molecular probes or biomarkers in the diagnosis of diseases, such as Alzheimer’s or Parkinson’s. Herein is reported the synthesis of five new pyrrole derivatives bearing phenyl rings on positions 1, 2, and 4, with electron-donating groups at the periphery. The introduction of more or stronger electron-donating groups red-shifts and increases the efficiency of the fluorescence emission.

Key words

triphenylpyrroles - Nef reaction - Paal–Knorr reaction - fluorescence - crystal structure

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690828.
  • Supporting Information
 

  • References and Notes

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