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Issue 15, 2017
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Dipolar vinyl sulfur fluorescent dyes. Synthesis and photophysics of sulfide, sulfoxide and sulfone based D–π–A compounds

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Abstract

New vinyl sulfides and sulfoxides were obtained in good yields using the Horner–Wadsworth–Emmons (HWE) reaction. The vinyl sulfides and sulfoxides presented preferentially the E-stereochemistry. The respective vinyl sulfones were obtained in good yields from the vinyl sulfides by a simple oxidation step using mCPBA, solely as the E isomers. These derivatives presented absorption maxima in the UV-A region with molar absorptivity coefficients and radiative rate constant values ascribed to spin and symmetry-allowed 1π–π* electronic transitions. Experimentally, a small solvatochromic effect indicated an almost absent charge transfer character in the ground-state. A fluorescence emission in the violet-green region with a significative redshift on the maxima with increasing solvent polarity was observed, which could be related to a better electron delocalization in the excited state, as a result of an intramolecular charge transfer state. DFT and TD-DFT calculations were performed at the PBE1PBE and CAM-B3LYP levels of theory. No solvatochromic effect was observed in the ground state, but a bathochromic effect was detected in the emission maxima. Starting from sulfides to sulfones, the addition of oxygen atoms improved the charge separation, enabling an ICT state, mainly in P3 and P5. This charge separation was more efficient in the triphenylamino derivatives than among the pyrene derivatives since the first one has a better electron-donating character.

Graphical abstract: Dipolar vinyl sulfur fluorescent dyes. Synthesis and photophysics of sulfide, sulfoxide and sulfone based D–π–A compounds

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Publication details

The article was received on 09 Dec 2016, accepted on 20 Jan 2017 and first published on 27 Jan 2017


Article type: Paper
DOI: 10.1039/C6RA27989A
RSC Adv., 2017,7, 8832-8842
  • Open access: Creative Commons BY-NC license
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    Dipolar vinyl sulfur fluorescent dyes. Synthesis and photophysics of sulfide, sulfoxide and sulfone based D–π–A compounds

    M. Monçalves, G. M. Zanotto, J. M. Toldo, D. S. Rampon, P. H. Schneider, P. F. B. Gonçalves, F. S. Rodembusch and C. C. Silveira, RSC Adv., 2017, 7, 8832
    DOI: 10.1039/C6RA27989A

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