A series of dansyl-based fluorescent probes bearing linear alkyl-1,n-diamine chains of different length (DA1.n, n = 2-8, 10, 12) was characterized in terms of the absorptive and emissive features in solvents of different polarity and hydrogen bond donor/hydrogen bond acceptor character. The probes show solvent-dependent absorption, a feature that is uncommon among dansyl derivatives. The dual emission of DA1.n probes is strong in non-aqueous solvents and is influenced by the chain length and interactions with the solvent. Solvent effects on the spectral parameters were rationalized on the basis of the Kamlet-Taft and Catalán solvatochromic models, in order to quantify the degree of polarity-driven and hydrogen bonding interactions. A comparative discussion of the results predicted by the two models was made. In ground state, the DA1.n probes act as hydrogen bond acceptors. In excited state, hydrogen bonding is less favoured, the solute-solvent interactions being governed by the increasing polarity of the solvent that results in a large bathochromic shift of the emission. A comparison was made with the spectral features previously reported for the corresponding series of bis-dansyl fluorescent probes (2DA1.n).
Keywords: Dansyl fluorophores; Dual fluorescence; Hydrogen bonding; Solvatochromism; Solvent polarity.
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