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Fluorescence Commutation and Surface Photopatterning with Porphyrin Tetradithienylethene Switches
Author(s) -
Biellmann Thomas,
Galanti Agostino,
Boixel Julien,
Wytko Jennifer A.,
Guerchais Véronique,
Samorì Paolo,
Weiss Jean
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201704222
Subject(s) - porphyrin , fluorescence , photochromism , photochemistry , free base , polystyrene , materials science , luminescence , absorption (acoustics) , chemistry , optoelectronics , optics , organic chemistry , polymer , salt (chemistry) , physics , composite material
Abstract Four tetradithienylethene (DTE) substituted porphyrins, the free base 1H 2 , and three metal derivatives ( 1Zn , 1Co , 1Ni ), were synthesized and studied. These dyads, for which the DTE units are connected to the porphyrin's meso positions via a meta ‐phenyl spacer, exhibit reversible photochromic properties in all cases, with conversion to the photostationary state (PSS) up to 88 %, as confirmed by absorption and NMR spectroscopies. Compounds 1H 2 and 1Zn are fluorescent in solution and display a red emission. Upon irradiation with UV light to trigger the closing of the DTEs, the fluorescence of both the free base and zinc porphyrin was very efficiently quenched in solution. The reversible, photo‐switching of luminescence was retained in a tetra‐DTE free‐base porphyrin‐doped polystyrene film, for which photo‐patterning was demonstrated by confocal scanning microscopy. The tunable fluorescent properties of this multi‐DTE framework render this compound of interest as a photo‐rewritable fluorescent ink.