Molecular switches
Light offers outstanding possibilities for external regulation in a plethora of applications, which are enabled by molecular photoswitches that change their properties in a reversible manner upon illumination. This Beilstein Journal of Organic Chemistry thematic issue will cover all aspects of molecular photoswitches, from their discovery, design and synthesis, through spectroscopic and computational characterization, all the way to applications in materials, biological systems, and beyond. Contributions are invited that provide new insights into all facets of this multidisciplinary topic, ranging from physical and organic chemistry all the way to the materials and life sciences.
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- Full Research Paper
- Published 26 Jun 2019
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Scheme 1: Light-responsive end-to-end assembly of host-functionalized gold nanorods (AuNR) by cyclodextrin–AA...
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Scheme 2: Two-step ligand exchange reaction for the synthesis of water-soluble cyclodextrin end-functionalize...
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Figure 1: a) ζ-Potential measurement of different stages of the ligand exchange. b) UV–vis spectroscopy befor...
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Figure 2: UV–vis spectroscopy of a) [tCD+tTEG]AuNR with different amount of dAAP (0-35 µM). b) [tCD]AuNR with...
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Figure 3: SPR maxima of [tCD+tTEG]AuNR with dAAP during four cycles of irradiation. a) Longitudinal SPR. b) T...
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Figure 4: TEM-BF images of a) [tCD+tTEG]AuNR. b and c) AuNR end-to-end assemblies by dAAP (15 µM). d) Dissolv...
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Figure 5: Reversible aggregation of [tCD+tTEG]AuNR by addition of dAAP (15 µM) monitored by dynamic light sca...
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- Full Research Paper
- Published 05 Jul 2019
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Figure 1: Structures of diazocine platform molecules (diazocine-TATAs) 1 and 2 in cis (1a, 2a) and trans-conf...
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Scheme 1: Synthesis route of para-diazocine platform molecule 1. a) Pd(dppf)Cl2, Cu(I)I, Et3N, 1 h, 60 °C; b)...
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Scheme 2: Synthesis route of meta-diazocine platform 2. a) 1: KOt-Bu, THF, 3 min, 0 °C, N2; 2: Br2, 5 min, 0 ...
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Figure 2: UV–vis spectra of 1 (left) and 2 (right) in THF at room temperature. Black: as synthesized, red: af...
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Figure 3: STM images (30 × 30 nm², Ubias = 0.3 V, It = 40 pA) of self-assembled monolayers of (a) compound 1 ...
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- Full Research Paper
- Published 30 Jul 2019
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Figure 1: Structures of the norbornadiene platform 1a and the quadricyclane platform 1b (for geometry coordin...
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Scheme 1: Syntheses of the norbornadiene TATA platform 1 and TOTA platform 3. a) TMS-acetylene, Pd(PPh3)4, Cu...
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Scheme 2: Synthesis of methylphenylnorbornadiene platform 2. a) Pd(PPh3)4, Na2CO3, toluene, EtOH, H2O, N2, re...
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Figure 2: UV–vis spectra of platform molecules 1 (a), 2 (b) and 3 (c) (in THF at rt): Norbornadiene (black), ...
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Figure 3: 1H NMR spectra of 1 in deuterated oxygen containing deuterated benzene (left) and degassed deuterat...
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Figure 4: Determination of the thermal isomerization rate k of 1b (QC) by 1H NMR spectroscopy (toluene, 293.5...
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Figure 5: (a) STM image of self-assembled monolayers of compound 1 on Au(111) (40 × 40 nm2, It = 0.05 nA, Ubi...
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- Letter
- Published 23 Aug 2019
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Scheme 1: a) Azobenzenes A1–3 employed in this study. b) U-shaped anthracene halogen bond acceptor bearing tw...
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Figure 1: Electrostatic potential map at different isodensity values (B3LYP/ def2/TZVP/DGZVP optimized geomet...
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Figure 2: Top: Vertical electronic absorption spectra of a) A2 and b) A3, calculated using TD-B3LYP/def2-TZVP...
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Figure 3: a) Space-filling model of U1···A2. The kinked alignment of both the lutidine units of U1 and the az...
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- Letter
- Published 13 Sep 2019
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Scheme 1: Reaction mechanisms of Huisgen cyclization catalyzed by Cu(I) and Ru(I).
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Scheme 2: Synthesis and photochromism of bisthiazolyltriazoles.
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Figure 1: Absorption spectral change of triazoles 1o–3o upon irradiation of 313 nm light in MeCN at 28 °C. Li...
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Scheme 3: Wavelengths of absorption maxima of the closed forms of bisthienyletenes in hexane [36].
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Scheme 4: Photochromism of closely related compounds.
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Figure 2: Absorption spectral change of triazoles 1c–3c during the thermal back reaction after 313-nm light i...
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Scheme 5: Bond length (a) (in Å) and Mulliken bond order (b) of 1c–3c obtained by DFT calculations. Top numbe...
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Scheme 6: Possible reaction mechanism of thermal ring opening of the closed forms.
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- Full Research Paper
- Published 16 Sep 2019
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Figure 1: Selisistat (1) and hit compound GW435821X (2a).
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Scheme 1: Reagents and conditions: a) appropriate boronic acid, Pd(PPh3)4, Na2CO3, DMF, H2O, microwave, 15 mi...
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Scheme 2: Reagents and conditions: a) Pd2(dba)3 or Pd(OAc)2, P(o-tol)3, TEA, DMF, 120–140 °C, 0.7–24 h, 11–75...
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Figure 2: (Left) UV–vis spectrum of 2b 50 µM in 5% DMSO (v/v) in assay buffer after varying durations of irra...
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Figure 3: (Left) LC chromatogram of the LC–HRMS analysis of 2b after varying durations of irradiation with 25...
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Scheme 3: Photocyclization and oxidation reaction of 2b upon UV irradiation.
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Figure 4: Calculated and experimental absorption spectra of compounds (E)-2b-B (A), (Z)-2b-A (B), and product...
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Scheme 4: Reagents and conditions: a) 4-fluoroaniline, oxone, HAc, 60 °C, 14 d, 42%; b) NH3, MeOH, rt, 3 d, 9...
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Figure 5: (Left) UV–vis spectrum of 11, 50 µM in 5% DMSO (v/v), in assay buffer at the thermal equilibrium an...
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Aggregation-induced emission effect on turn-off fluorescent switching of a photochromic diarylethene
- Full Research Paper
- Published 20 Sep 2019
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Figure 1: Synthetic procedure for a diarylethene (1o).
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Figure 2: Photochromic reaction of diarylethene 1o having an ESIPT moiety.
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Figure 3: Absorption spectral changes of diarylethene 1o having an ESIPT moiety in THF (c = 1.3×10-5 M). Blac...
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Figure 4: Fluorescent spectra of 1o in several solvents (λex = 370 nm). Hexane (black line), chloroform (red ...
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Figure 5: (a) The energy diagram of the ESIPT process of 1. (b) ESIPT fluorescence quenching upon UV light (λ...
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Figure 6: (a) Fluorescence photographs of solutions/suspensions of 1o (1.2×10-4 M) in THF/water mixtures with...
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Figure 7: (a) Crystals of 1o before UV light irradiation, (b) Green fluorescence of 1o observed under UV ligh...
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