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The pyrenylindole was inserted into a peptide by solid\u2010phase coupling, with use of a 2\u2010chlorotrityl chloride resin and a Fmoc strategy. The photophysical properties of the pyrenylindole and phenalenoindole in several solvents were studied and showed that these compounds can be used as fluorescence probes. The results obtained with the peptide labelled with the pyrenylindole moiety show potential for use of this compound as a fluorescence label avoiding the aggregation propensity of pyrene compounds. Photophysical studies of the pyrenylindole and of the phenalenoindole in lipid membranes were also carried out. Steady\u2010state fluorescence anisotropy measurements revealed that both compounds adopt locations inside the lipid bilayers and are able to report the transition between the gel and liquid\u2010crystalline phases. The results point to potential use of these compounds as fluorescent probes for biological systems.(\u00a9 Wiley\u2010VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2009)<\/jats:p>","DOI":"10.1002\/ejoc.200900351","type":"journal-article","created":{"date-parts":[[2009,6,29]],"date-time":"2009-06-29T12:05:54Z","timestamp":1246277154000},"page":"3906-3916","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Synthesis and Photophysical Studies of a Pyrenylindole and a Phenalenoindole Obtained from Dehydroamino Acid Derivatives \u2013 Application as Fluorescent Probes for Biological Systems"],"prefix":"10.1002","volume":"2009","author":[{"given":"Goreti","family":"Pereira","sequence":"first","affiliation":[]},{"given":"Ana S.","family":"Abreu","sequence":"additional","affiliation":[]},{"given":"Elisabete M. S.","family":"Castanheira","sequence":"additional","affiliation":[]},{"given":"Paulo J. G.","family":"Coutinho","sequence":"additional","affiliation":[]},{"given":"Paula M. 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