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The peptide sequences comprise two nonproteinogenic residues: a \u03b2\u2010(1\u2010azulenyl)\u2010<jats:sc>L<\/jats:sc>\u2010alanine (Aal) residue, obtained by formally functionalizing the Ala side chain with the azulene chromophore, and a C<jats:sup>\u03b1<\/jats:sup>\u2010tetrasubstituted \u03b1\u2010amino acid (TOAC), incorporating a nitroxide group in a cycloalkyl moiety. Aal represents a new fluorescent, quasi\u2010isosteric Trp analog and TOAC a stable radical species, frequently used as a paramagnetic probe in biochemical studies. The peptide chains differ in the sequence position of the two probes and are heavily based on Aib (\u03b1\u2010aminoisobutyric acid) residues to generate conformationally restricted helical structures, as confirmed by both spectroscopic and computational results. The conformationally controlled, excited state interactions, determining the photophysical relaxation of the Aal*\/TOAC pair, are also discussed. \u00a9 2004 Wiley Periodicals, Inc. 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