A Modern Look at Spiropyrans: From Single Molecules to Smart Materials

Kozlenko, Anastasia S.; Ozhogin, Ilya V.; Pugachev, A. D.; Lukyanova, M. B.; El-Sewify, Islam M.; Lukyanov, B. S.

doi:10.1007/s41061-022-00417-2

Cited by 37 publications

(32 citation statements)

References 421 publications

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“…Regarding other photoswitches (e.g., spiropyrans, dithienylethenes, and donor-acceptor Stenhouse adducts), the interested reader is referred to previous extensive reviews. [31][32][33] Finally, photochromic tethered ligands, [18] photoswitchable peptides [34] or nucleic acids [35] are outside the scope of this review.…”

Section: Introductionmentioning

confidence: 99%

“…Because a large number of references was necessary to categorize and identify trends within the field, the focus of the current analysis is on studies that report the use of molecular photoswitches that operate through the E‐Z isomerization of a double bond. Regarding other photoswitches (e.g., spiropyrans, dithienylethenes, and donor‐acceptor Stenhouse adducts), the interested reader is referred to previous extensive reviews [31–33] . Finally, photochromic tethered ligands, [18] photoswitchable peptides [34] or nucleic acids [35] are outside the scope of this review.…”

Section: Introductionmentioning

confidence: 99%

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Rational Design in Photopharmacology with Molecular Photoswitches

et al. 2023

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Photopharmacology is an attractive approach for achieving targeted drug action with the use of light. In photopharmacology, molecular photoswitches are introduced into the structure of biologically active small molecules to allow for the optical control of their potency. Going beyond trial and error, photopharmacology has progressively applied rational drug design methodologies to devise light-controlled bioactive ligands. In this review, we categorize photopharmacological efforts from the standpoint of medicinal chemistry strategies, focusing on diffusible photochromic ligands modified with photoswitches that operate through E-Z bond isomerization. In the vast majority of cases, photoswitchable ligands are designed as analogs of existing compounds, through a variety of approaches. By analyzing in detail a comprehensive list of instructive examples, we describe the state of the art and discuss future opportunities for rational design in photopharmacology.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Rational Design in Photopharmacology with Molecular Photoswitches

et al. 2023

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“…Photochromic materials are widely used in sensing, optoelectronics and anti-counterfeiting due to their photoinduced coloring and reversible color-bleaching properties. 1–3 Photochromic organic complexes, such as azobenzene, 4,5 spiropyran, 6,7 viologen 8,9 and their derivatives, can achieve reversible color changes rapidly in response to ultraviolet light. In contrast to other organic photochromic molecules, viologen compounds achieve their reversible color change through a redox mechanism.…”

Section: Introductionmentioning

confidence: 99%

A novel ZnO/viologen photochromic composite film with a rapid UV response for rewritable paper, solar UV detection, smart windows and anti-counterfeiting

et al. 2023

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“…In this Review, we will focus only on the first scenario – i.e ., only on photoinduced proton transfer phenomena [36] in water. We suggest the readers interested in other physicochemical properties and applications to consult other more comprehensive reviews [3,31,37–41] …”

Section: Introductionmentioning

confidence: 99%

“…We suggest the readers interested in other physicochemical properties and applications to consult other more comprehensive reviews. [3,31,[37][38][39][40][41]…”

Section: Introductionmentioning

confidence: 99%

Photoacidity of Indolinospirobenzopyrans in Water

Berton

Pezzato

2023

Eur J Org Chem

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Cristian Pezzato was nominated to be part of the #NextGenOrgChem collection by EurJOC Board Member Maria Valeria D'AuriaThe reversible isomerism of indolinospirobenzopyrans is perhaps among the most studied phenomena in the field of molecular switches. Although they began to gain attention as early as 70 years ago following the seminal work of Hirshberg and Fischer, who were the first to recognize their photochromic behaviours, their implementation as photoacids emerged prominently only in the last decade. In this Review, we contextualize the prerequisites underlying the photo-triggered proton release that occurs in these molecular switches, highlighting the most recent advances in their characterization and application as "metastable-state photoacids" in water.[ + ] Cristian Pezzato was nominated to be part of this collection by EurJOC Board Member Maria Valeria D'Auria.

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A Modern Look at Spiropyrans: From Single Molecules to Smart Materials

Cited by 37 publications

References 421 publications

Rational Design in Photopharmacology with Molecular Photoswitches

Rational Design in Photopharmacology with Molecular Photoswitches

A novel ZnO/viologen photochromic composite film with a rapid UV response for rewritable paper, solar UV detection, smart windows and anti-counterfeiting

Photoacidity of Indolinospirobenzopyrans in Water

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