Thermal and Photochemical Properties of 4′,7‐Dihydroxyflavylium in Water–Ionic Liquid Biphasic Systems: A Write–Read–Erase Molecular Switch

Pina, Fernando; Lima, Jorge; Parola, A. Jorge; Afonso, Carlos A. M.

doi:10.1002/ange.200353131

Cited by 10 publications

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“…Other families of derivatives from which 2-hydroxychalcones originate include deoxyanthocyanidins and natural and synthetic flavylium compounds, ,,, also undergo reactions reported in Scheme . The interest of 2-hydroxychalcones is thus related to their peculiar photochromic system exhibiting multistate, multifunctional characteristics. − ,, …”

Section: Introductionmentioning

confidence: 99%

Photochemistry of 7-Hydroxy-2-(4-hydroxystyryl)-1-benzopyrylium and Related Compounds

et al. 2008

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2-Styryl-1-benzopyrylium derivatives exhibit deeper hues and absorption spectra that are substantially red-shifted when compared with their 2-phenyl-1-benzopyrylium analogues. They follow the same pH and light-dependent network of chemical reactions previously described for 2-phenyl-1-benzopyrylium compounds. In this work, the photochromic properties of 7-hydroxy-2-(4-hydroxystyryl)-1-benzopyrylium chloride are reported. This compound was fully characterized by UV-vis absorption, fluorescence emission, pH jumps, and flash photolysis, and its properties were compared with the analogue 7,4'-dihydroxyflavylium (7-hydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium). The trans-chalcones of both compounds lacking the hydroxyl in position 2 were synthesized and used as model compounds since they exhibit cis-trans isomerization but cannot be involved in the other processes resulting from the ring closure. The transient absorption of two triplets attributed to the chalcones Ct/Ct(-), and a tautomer was detected by nanosecond flash photolysis, independent of the existence of the 2-hydroxyl substituent. The experimental results are compatible with the main formation of cis-chalcone from the singlet state. In the case of the styryl derivatives, the fraction of triplet formed from excitation of Ct is much higher, and the fraction of isomerization is much smaller. For this reason, the photochemistry of 7-hydroxy-2-(4-hydroxystyryl)-1-benzopyrylium in water is much less efficient than that of its parent 7,4'-dihydroxyflavylium; however, in the presence of CTAB micelles, intense red colors can be obtained upon irradiation, confirming the usefulness of this family of compounds as photochromic systems.

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Section: Introductionmentioning

confidence: 99%

Photochemistry of 7-Hydroxy-2-(4-hydroxystyryl)-1-benzopyrylium and Related Compounds

et al. 2008

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Molecular Logic Gates

Szaciłowski

2012

Infochemistry

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Multiple Addressing in a Hybrid Biphotochromic System

Frigoli

Mehl

2005

Angewandte Chemie

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Vier ungleiche Brüder: Ein aus einer Naphthopyran‐ und einer Diaryletheneinheit bestehendes biphotochromes System (1) bildet vier Zustände mit ganz unterschiedlichem Absorptionsverhalten. Das Öffnen des Naphthopyranrings hat Konjugation und elektronische Verknüpfung der beiden Photochrome zur Folge, das Schließen des offenen Diarylethensystems dehnt das π‐Elektronensystem über das ganze Molekül aus.

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Thermal and Photochemical Properties of 4′,7‐Dihydroxyflavylium in Water–Ionic Liquid Biphasic Systems: A Write–Read–Erase Molecular Switch

Cited by 10 publications

References 29 publications

Photochemistry of 7-Hydroxy-2-(4-hydroxystyryl)-1-benzopyrylium and Related Compounds

Photochemistry of 7-Hydroxy-2-(4-hydroxystyryl)-1-benzopyrylium and Related Compounds

Molecular Logic Gates

Multiple Addressing in a Hybrid Biphotochromic System

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