2023
DOI: 10.1039/d3ob00413a
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Twelve-membered ring photoswitches with excellentZEconversion under ambient light

Abstract: Incorporation of azobenzenes in macrocycles is an intriguing approach for fine tuning the photophysical properties of these photoswitches and tailoring them to specific applications. A versatile synthesis of macrocyclic azobenzenes...

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Cited by 6 publications
(5 citation statements)
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“…The group of von Krbek followed with the syntheses of a series of ortho-and para-substituted "all-carbon" bridged twelvemembered azomacrocycles in a conceived synthetic route (Figure 10c). [56] While ortho-alkyl-and acyl-substituted azomacrocycles were accessible by oxidative coupling of the unsubstituted macrocycle, para-substituted azomacrocycles were synthesised starting from the para-iodo azomacrocycle by coupling reactions, showcasing a convenient and expandable approach for post-modification. In line with the results from Staubitz and co-workers, none of the investigated substitution patterns increased the PSS distribution compared to the parent systems.…”
Section: Geometry Changementioning
confidence: 99%
See 1 more Smart Citation
“…The group of von Krbek followed with the syntheses of a series of ortho-and para-substituted "all-carbon" bridged twelvemembered azomacrocycles in a conceived synthetic route (Figure 10c). [56] While ortho-alkyl-and acyl-substituted azomacrocycles were accessible by oxidative coupling of the unsubstituted macrocycle, para-substituted azomacrocycles were synthesised starting from the para-iodo azomacrocycle by coupling reactions, showcasing a convenient and expandable approach for post-modification. In line with the results from Staubitz and co-workers, none of the investigated substitution patterns increased the PSS distribution compared to the parent systems.…”
Section: Geometry Changementioning
confidence: 99%
“…a) Isomerisation of photoswitchable macrocycle 30 as reported by Staubitz and colleagues and structure motifs which were functionalised with different residues reported by the groups of b) Staubitz [55] and c) von Krbek. [56] Figure 11. Structures of porphyrin macrocycles 31 to 33.…”
Section: Geometry Changementioning
confidence: 99%
“…16 Of the various classes of photoswitches, 17,18 those that display a photoinduced trans-cis (E/Z) isomerism are arguably the most commonly studied. 3,[19][20][21][22][23][24] Examples of such switches include derivatives of stilbene (C] C), 25,26 azobenzene and diazocine (N]N), [19][20][21]27,28 and subsets of imines (C]N) that include hydrazones 29 and acylhydrazones. 22,30 Imines, specically sterically hindered benzilderived imines, 31 ketimines 32-34 and iminothioindoxyls 3,35 have shown promise as photoswitches and light-activated molecular motors that display unidirectional rotation about the imine bond.…”
Section: Introductionmentioning
confidence: 99%
“…[33] That this macrocycle cannot easily be adapted to a system with higher half-life times was also found by K. S. von Krbek and coworkers who replaced the oxygen atoms by methylene groups; this gave a half-life time of 19 h at 45 °C in DMF. [34] Based on studies demonstrating extended half-life times of Zazobenzenes with fluorine substituents, [28,35] our objective was to systematically introduce fluorine atoms into the HOAM ring. This approach aimed to combine the influence of the fluorine atoms with the inherent ring strain to develop molecular switches exhibiting prolonged half-lives.…”
Section: Introductionmentioning
confidence: 99%