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Search for "photoswitch" in Full Text gives 31 result(s) in Beilstein Journal of Organic Chemistry.

Switchable molecular tweezers: design and applications

  • Pablo Msellem,
  • Maksym Dekthiarenko,
  • Nihal Hadj Seyd and
  • Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

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  • first part will be devoted to chemically responsive tweezers, including stimuli such as pH, metal coordination, and anion binding. Then, redox-active and photochemical tweezers will be presented. Keywords: coordination; molecular recognition; molecular switches; photoswitch; redox; supramolecular
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Published 01 Mar 2024

Substituted nitrogen-bridged diazocines

  • Pascal Lentes,
  • Jeremy Rudtke,
  • Thomas Griebenow and
  • Rainer Herges

Beilstein J. Org. Chem. 2021, 17, 1503–1508, doi:10.3762/bjoc.17.107

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  • makes them promising candidates for applications in photopharmacology. The halogen substituents allow further functionalization via cross-coupling reactions. Keywords: bridged azobenzene; diazocine; photopharmacology; photoswitch; triazocine; visible light switch; water-soluble switch; Introduction
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Published 25 Jun 2021

Synthesis of 4-substituted azopyridine-functionalized Ni(II)-porphyrins as molecular spin switches

  • Jannis Ludwig,
  • Tobias Moje,
  • Fynn Röhricht and
  • Rainer Herges

Beilstein J. Org. Chem. 2020, 16, 2589–2597, doi:10.3762/bjoc.16.210

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  • )-porphyrins; photoswitch; record player molecules; spin state; spin switch; Introduction Molecular spin switches operated with visible light in homogeneous solution [1] or on surfaces [2], hold promise for a number of hitherto unprecedented applications such as switchable contrast agents [3][4][5][6][7
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Published 21 Oct 2020

Azo-dimethylaminopyridine-functionalized Ni(II)-porphyrin as a photoswitchable nucleophilic catalyst

  • Jannis Ludwig,
  • Julian Helberg,
  • Hendrik Zipse and
  • Rainer Herges

Beilstein J. Org. Chem. 2020, 16, 2119–2126, doi:10.3762/bjoc.16.179

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  • activity. The rate constants in the two switching states differ by a factor of 2.2, and the catalytic switching is reversible. Keywords: catalysis; Ni(II)-porphyrins; nucleophilic catalyst; photoswitch; record player molecules; spin switch; Introduction Photoswitchable catalysis has been realized
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Published 31 Aug 2020

Potent hemithioindigo-based antimitotics photocontrol the microtubule cytoskeleton in cellulo

  • Alexander Sailer,
  • Franziska Ermer,
  • Yvonne Kraus,
  • Rebekkah Bingham,
  • Ferdinand H. Lutter,
  • Julia Ahlfeld and
  • Oliver Thorn-Seshold

Beilstein J. Org. Chem. 2020, 16, 125–134, doi:10.3762/bjoc.16.14

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  • molecular photoswitch that has only recently been applied as a photoswitchable pharmacophore for control over bioactivity in cellulo. Uniquely, in contrast to other photoswitches that have been applied to biology, the pseudosymmetric hemithioindigo scaffold has allowed the creation of both dark-active and
  • addressable by photopharmacology. Keywords: antimitotics; cytoskeleton; hemithioindigo; photopharmacology; photoswitch; Introduction The cytoskeletal scaffolding protein tubulin, a heterodimer consisting of α and β subunits, each of various isotypes, reversibly assembles into giant non-covalent polymeric
  • , all-visible-light photoswitching. Results and Discussion Design strategy for HTIs The HTI-based colchicinoid HOTubs (e.g., HOTub-31) that we previously explored had the HTI photoswitch embedded inside a methoxylation pattern, such that one isomer obeyed the structure–activity relationship (SAR) of
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Published 27 Jan 2020

Light-controllable dithienylethene-modified cyclic peptides: photoswitching the in vivo toxicity in zebrafish embryos

  • Sergii Afonin,
  • Oleg Babii,
  • Aline Reuter,
  • Volker Middel,
  • Masanari Takamiya,
  • Uwe Strähle,
  • Igor V. Komarov and
  • Anne S. Ulrich

Beilstein J. Org. Chem. 2020, 16, 39–49, doi:10.3762/bjoc.16.6

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  • , (iii) demonstrate photoswitching of the whole-body toxicity for the dithienylethene-modified peptides in vivo, (iv) re-analyze previous structure–toxicity relationship data, and (v) select promising candidates for potential clinical development. Keywords: diarylethene photoswitch; gramicidin S
  • peptides [19][20][21]. The idea behind photopharmacology is based on the design and use of drugs containing a reversibly photoisomerizable fragment (“molecular photoswitch”) as part of their structure. Importantly, the photoisomerizable fragment should – in one of its photoforms – destroy or mask the
  • photoswitch into the backbone of gramicidin S (1, GS), which is an intrinsically biostable cyclic peptide, as exemplified by one of our first prototypes compound 2 (Figure 1C). This natural antimicrobial agent has an amphipathic structure, whose functional mechanism is attributed to the permeabilization of
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Published 07 Jan 2020

Starazo triple switches – synthesis of unsymmetrical 1,3,5-tris(arylazo)benzenes

  • Andreas H. Heindl and
  • Hermann A. Wegner

Beilstein J. Org. Chem. 2020, 16, 22–31, doi:10.3762/bjoc.16.4

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  • of multiple AB units into one molecule allows to access multiple states upon isomerization, which dramatically increases the potential for information storage using this photoswitch. Ideally, one molecule can be treated with multiple different inputs, leading to defined, detectable outputs. An
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Published 03 Jan 2020

Synthesis and characterization of bis(4-amino-2-bromo-6-methoxy)azobenzene derivatives

  • David Martínez-López,
  • Amirhossein Babalhavaeji,
  • Diego Sampedro and
  • G. Andrew Woolley

Beilstein J. Org. Chem. 2019, 15, 3000–3008, doi:10.3762/bjoc.15.296

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  • ; azonium; molecular switches; ortho substitution; photoisomerization; photoswitch; visible light; Introduction The application of photoswitches to control biological targets has been a driving force for the development of photoswitches that operate at wavelengths that are compatible with cells and tissues
  • in an aqueous solution, it is useful as a photoswitch for the photocontrol of biomolecules [6]. It absorbs red light, undergoes trans-to-cis photoisomerization, and relaxes to the trans isomer in the dark on the timescale of seconds so that pulses of red light can be used to drive multiple
  • isomerization cycles [10]. Efforts to apply 1 to photocontrol protein–protein interactions have recently been reported [13]. Despite the usefulness of 1 as a photoswitch, compounds undergoing photoisomerization at longer wavelengths (>700 nm) would be valuable since the penetration of light through tissue is
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Published 30 Dec 2019

Design, synthesis and investigation of water-soluble hemi-indigo photoswitches for bioapplications

  • Daria V. Berdnikova

Beilstein J. Org. Chem. 2019, 15, 2822–2829, doi:10.3762/bjoc.15.275

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  • solubility of the photoswitch and increases the red shift of the absorption maximum of the E-isomer. As a further step, the synthetic approach towards the attachment of the RNA-affine alkylamino substituent was developed. Overall, the hemi-indigo derivatives were introduced as promising photoswitches for
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Published 22 Nov 2019

Chemical tuning of photoswitchable azobenzenes: a photopharmacological case study using nicotinic transmission

  • Lorenzo Sansalone,
  • Jun Zhao,
  • Matthew T. Richers and
  • Graham C. R. Ellis-Davies

Beilstein J. Org. Chem. 2019, 15, 2812–2821, doi:10.3762/bjoc.15.274

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  • glutathione. However, attempts to conjugate with a cysteine on a genetically modified nicotinic acetylcholine receptor did not afford the expected light-responsive channel. Our data indicate that the 4FAB photoswitch can be derivatized bifunctionally for genetically-targeted photopharmacology whilst
  • regular AB-based photoswitch called "MAHoCh" [16]. The MAHoCh probe was originally designed [16] to activate nicotinic acetylcholine receptors in vivo. However, it was found that the trimethylammonium (TA) head group blocked acetylcholine binding when the photoprobe was cross-linked to the channel near
  • % overall yield. Installation of the cationic head was performed in two steps: first bromination of 11 via Appel reaction, followed by treatment with trimethylamine to give 2 in 35% overall yield. Photoswitch 2 is the first example of a bifunctional, asymmetrically substituted 4FAB chromophore that actually
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Published 21 Nov 2019

Photoreversible stretching of a BAPTA chelator marshalling Ca2+-binding in aqueous media

  • Aurélien Ducrot,
  • Arnaud Tron,
  • Robin Bofinger,
  • Ingrid Sanz Beguer,
  • Jean-Luc Pozzo and
  • Nathan D. McClenaghan

Beilstein J. Org. Chem. 2019, 15, 2801–2811, doi:10.3762/bjoc.15.273

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  • μM, respectively). Reversible photoliberation/uptake leading to a variation of free calcium concentration in solution was detected using a fluorescent Ca2+ chemosensor. Keywords: azobenzene; BAPTA; calcium binding; photorelease; photoswitch; Introduction In terms of synthetic calcium binding
  • EDTA) such that photoswitching would enhance or lower Ca2+ binding based on the state of the adjacent photoswitch. Photogeneration of a positive charge proximal to the BAPTA site is undoubtedly the most robust approach to provoke calcium cation release, while diminishing electron density on the
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Published 21 Nov 2019

A combinatorial approach to improving the performance of azoarene photoswitches

  • Joaquin Calbo,
  • Aditya R. Thawani,
  • Rosina S. L. Gibson,
  • Andrew J. P. White and
  • Matthew J. Fuchter

Beilstein J. Org. Chem. 2019, 15, 2753–2764, doi:10.3762/bjoc.15.266

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  • = 10 days), whereas 4pzMe-Cl2 (t1/2 ≈ 1 day) exhibits a reduction in half-life. Additionally, 4pzH-F2 boasts a vastly increased thermal half-life of 46 years over 4pzH (t1/2 = 1000 days) making it the longest-lived azoheteroarene photoswitch reported in the literature to date. This result demonstrates
  • °) to 4pzMe-Cl1 (127°) and to 4pzMe-Cl2 (113°; Figure 4). The effect of ortho-substitution on photoconversion efficiency To a first approximation, in order to achieve high Z–E photoconversion efficiency, the two isomers of an azo photoswitch must offer well-separated absorption bands. Most frequently, E
  • . Thus, a tilting of the pyrazole moiety away from orthogonality with respect to the plane generated by the aryl ring leads the n–π* excitation to be symmetry-allowed, with the corresponding increase in intensity. For example, the heteroring in fluorine-substituted 4pzH-F2 photoswitch is tilted with a θ
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Published 14 Nov 2019

A toolbox of molecular photoswitches to modulate the CXCR3 chemokine receptor with light

  • Xavier Gómez-Santacana,
  • Sabrina M. de Munnik,
  • Tamara A. M. Mocking,
  • Niels J. Hauwert,
  • Shanliang Sun,
  • Prashanna Vijayachandran,
  • Iwan J. P. de Esch,
  • Henry F. Vischer,
  • Maikel Wijtmans and
  • Rob Leurs

Beilstein J. Org. Chem. 2019, 15, 2509–2523, doi:10.3762/bjoc.15.244

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  • VUF16216, a compound we have previously communicated as a small-molecule efficacy photoswitch for the peptidergic chemokine GPCR CXCR3. A series of photoswitchable azobenzene ligands was prepared through various synthetic strategies and multistep syntheses. Photochemical and pharmacological properties were
  • pharmacological alternative, especially with respect to spatial and temporal precision [1][2]. Photochromic ligands usually contain a molecular photoswitch (photoswitchable moiety) that under certain wavelengths of illumination undergoes an isomerization event, thereby changing the properties of the molecule and
  • by large peptides CXCL9, CXCL10 and CXCL10 and involved in inflammatory responses. In fact, the six compounds reported in that study represent the first photochromic small-molecule class that harbors a dynamic efficacy photoswitch (from antagonism to agonism) on a peptidergic GPCR (Figure 1B). Here
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Published 23 Oct 2019

In search of visible-light photoresponsive peptide nucleic acids (PNAs) for reversible control of DNA hybridization

  • Lei Zhang,
  • Greta Linden and
  • Olalla Vázquez

Beilstein J. Org. Chem. 2019, 15, 2500–2508, doi:10.3762/bjoc.15.243

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  • first compounds here reported, may find applications in different fields such as chemical biology, nanotechnology and materials science. Keywords: azobenzene; hemithioindigo; peptide nucleic acid (PNA); photoswitch; visible-light irradiation; Introduction Light-driven control of oligonucleotide
  • translation [24][25]. Except a handful of current examples [22][24][26], most of these photoresponsive oligonucleotides are canonical ones where the classical azobenzene is the prominently used photoswitch; although spiropyrans [27], stilbenes [28], diarylethanes [29] and overcrowded alkenes [30] have also
  • used, we gained versatility using the divergent linear approach introduced by Seitz (Scheme 1) [42]. This strategy enabled the straightforward access to functionalized PNA via on-resin coupling of the corresponding photoswitch in good yields. Of note, this post-synthetic modification is compatible with
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Published 22 Oct 2019

Ultrafast processes triggered by one- and two-photon excitation of a photochromic and luminescent hydrazone

  • Alessandro Iagatti,
  • Baihao Shao,
  • Alberto Credi,
  • Barbara Ventura,
  • Ivan Aprahamian and
  • Mariangela Di Donato

Beilstein J. Org. Chem. 2019, 15, 2438–2446, doi:10.3762/bjoc.15.236

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  • – Istituto Nazionale di Ottica, Largo Enrico Fermi 6, 50125 Firenze, Italy 10.3762/bjoc.15.236 Abstract In this work we apply a combination of steady state and time resolved luminescence and absorption spectroscopies to investigate the excited-state dynamics of a recently developed molecular photoswitch
  • drawbacks still remain, calling for the development of new systems with improved behavior. Although the properties of a successful photoswitch have to be tailored on the application for which it is designed, there are several aspects whose improvement can be of benefit on a general basis. Major concerns on
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Published 15 Oct 2019

Excited state dynamics for visible-light sensitization of a photochromic benzil-subsituted phenoxyl-imidazolyl radical complex

  • Yoichi Kobayashi,
  • Yukie Mamiya,
  • Katsuya Mutoh,
  • Hikaru Sotome,
  • Masafumi Koga,
  • Hiroshi Miyasaka and
  • Jiro Abe

Beilstein J. Org. Chem. 2019, 15, 2369–2379, doi:10.3762/bjoc.15.229

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  • photoswitch molecules, the phenoxyl-imidazolyl radical complex (PIC) is a recently developed thermally reversible photochromic molecule whose thermal back reaction can be tuned from tens of nanoseconds to tens of seconds by rational design of the molecular structure. While the wide range of tunability of the
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Published 04 Oct 2019

Mono- and bithiophene-substituted diarylethene photoswitches with emissive open or closed forms

  • A. Lennart Schleper,
  • Mariano L. Bossi,
  • Vladimir N. Belov and
  • Stefan W. Hell

Beilstein J. Org. Chem. 2019, 15, 2344–2354, doi:10.3762/bjoc.15.227

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  • oxidized DAEs. However, due to poor emission, SyTh1 was not considered as a fluorescence marker. Another promising compound for applications in super-resolution microscopy was DAE AsOTh1. A high emission efficiency and a relatively fast cycloreversion, makes it a good candidate for a photoswitch applicable
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Published 01 Oct 2019

Azologization and repurposing of a hetero-stilbene-based kinase inhibitor: towards the design of photoswitchable sirtuin inhibitors

  • Christoph W. Grathwol,
  • Nathalie Wössner,
  • Sören Swyter,
  • Adam C. Smith,
  • Enrico Tapavicza,
  • Robert K. Hofstetter,
  • Anja Bodtke,
  • Manfred Jung and
  • Andreas Link

Beilstein J. Org. Chem. 2019, 15, 2170–2183, doi:10.3762/bjoc.15.214

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  • ‐time photomodulation of sirtuins in vitro. Keywords: azo compounds; epigenetics; photoswitch; sirtuins; stilbenes; Introduction Sirtuins are protein deacylases that cleave off not only acetyl, but also other acyl groups from the ε-amino group of lysines in histones and many other substrate proteins
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Published 16 Sep 2019

Insertion of [1.1.1]propellane into aromatic disulfides

  • Robin M. Bär,
  • Gregor Heinrich,
  • Martin Nieger,
  • Olaf Fuhr and
  • Stefan Bräse

Beilstein J. Org. Chem. 2019, 15, 1172–1180, doi:10.3762/bjoc.15.114

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  • can lead to improved properties, e.g., increased water-solubility of drug candidates [2] or the electronical separation of a photoswitch and a chromophore [6]. Often used moieties for these kinds of applications are triptycenes, cubanes, bicyclo[2.2.2]octanes (BCOs) and bicyclo[1.1.1]pentanes (BCPs
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Published 28 May 2019

Azologization of serotonin 5-HT3 receptor antagonists

  • Karin Rustler,
  • Galyna Maleeva,
  • Piotr Bregestovski and
  • Burkhard König

Beilstein J. Org. Chem. 2019, 15, 780–788, doi:10.3762/bjoc.15.74

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  • photo-induced trans–cis isomerization representing the time of birth of the azobenzene photoswitch. Benefiting of their accessible synthesis, large change in polarity and geometry upon switching, excellent photochromic properties and tuneability, azobenzenes are amongst the most widely used photochromic
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Published 25 Mar 2019

Oxidative and reductive cyclization in stiff dithienylethenes

  • Michael Kleinwächter,
  • Ellen Teichmann,
  • Lutz Grubert,
  • Martin Herder and
  • Stefan Hecht

Beilstein J. Org. Chem. 2018, 14, 2812–2821, doi:10.3762/bjoc.14.259

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  • reduction wave is shifted to lower potentials compared to C2+ for all observed cases by up to >600 mV (see Table S1, Supporting Information File 1). 2) The amount of FP2+ formed depends on both the electronic structure of the photoswitch and the scan rate. While at slow scan rates (10 mV s−1) the conversion
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Published 09 Nov 2018

Tetrathiafulvalene – a redox-switchable building block to control motion in mechanically interlocked molecules

  • Hendrik V. Schröder and
  • Christoph A. Schalley

Beilstein J. Org. Chem. 2018, 14, 2163–2185, doi:10.3762/bjoc.14.190

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  • reported (Figure 16) [85]. However, the axle bears a central azobenzene photoswitch, who’s E/Z-transitions can be controlled by light. The redox-switchable shuttle works as previously described and the position of the wheel can be controlled by oxidation or reduction. However, the configuration of the
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Published 20 Aug 2018

The role of alkyl substituents in deazaadenine-based diarylethene photoswitches

  • Christopher Sarter,
  • Michael Heimes and
  • Andres Jäschke

Beilstein J. Org. Chem. 2016, 12, 1103–1110, doi:10.3762/bjoc.12.106

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  • DNA photoswitches for the application in bionanotechnology and synthetic biology. Keywords: diarylethene; nucleoside; electrocyclic rearrangement; photochromism; photoswitch; Introduction Most biomacromolecules are per se not responsive to light. Their conversion into photoresponsive molecules opens
  • in which a purine nucleobase represented one of the aryl rings of the photoswitch (Figure 1B). Importantly and different from most other approaches towards photoswitchable nucleic acids, the nucleobase constituted an active part of the photoswitch (rather than an appendage), changing its bonding and
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Published 01 Jun 2016

Photoswitchable precision glycooligomers and their lectin binding

  • Daniela Ponader,
  • Sinaida Igde,
  • Marko Wehle,
  • Katharina Märker,
  • Mark Santer,
  • David Bléger and
  • Laura Hartmann

Beilstein J. Org. Chem. 2014, 10, 1603–1612, doi:10.3762/bjoc.10.166

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  • ; multivalent glycosystems; photoswitch; precision polymer; Introduction Carbohydrate ligand–receptor interactions underpin many important processes in biology, for example in host-pathogen interactions [1][2]. Although monosaccharides usually exhibit only low binding affinities, nature is able to obtain high
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Published 15 Jul 2014

Amino-substituted diazocines as pincer-type photochromic switches

  • Hanno Sell,
  • Christian Näther and
  • Rainer Herges

Beilstein J. Org. Chem. 2013, 9, 1–7, doi:10.3762/bjoc.9.1

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  • isomer is more stable than the trans form. Compared to the parent EBAB, which is a very efficient photoswitch, the conversion from the cis to the trans isomer upon irradiation with 405 nm is reduced to 34% (diamino derivative 4) and 54% (diacetamido derivative 5, cf. 92% in the parent compound). The
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Published 02 Jan 2013
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