Synthesis of N-acetyl diazocine derivatives via cross-coupling reaction

• Thomas Brandt,
• Pascal Lentes,
• Jeremy Rudtke,
• Michael Hösgen,
• Christian Näther and
• Rainer Herges

Beilstein J. Org. Chem. 2025, 21, 490–499, doi:10.3762/bjoc.21.36

• diazocine drop significantly in aqueous media, the corresponding quantum yields of the N-acetyl diazocine stay the same or even slightly improve (Table 1). In general, the quantum yields of parent diazocine and its’ nitrogen bridged derivative exceed the quantum yields of other molecular photoswitches like

Effect of substitution position of aryl groups on the thermal back reactivity of aza-diarylethene photoswitches and prediction by density functional theory

• Misato Suganuma,
• Daichi Kitagawa,
• Shota Hamatani and
• Seiya Kobatake

Beilstein J. Org. Chem. 2025, 21, 242–252, doi:10.3762/bjoc.21.16

• Molecular photoswitches have been studied for a long time because their physicochemical properties such as refractive index [1][2], dipole moment [3][4], conductivity [5][6], magnetism [7][8], and fluorescence [9][10][11] can be spatiotemporally modulated by light without physical contact. Therefore

• , various application examples of molecular photoswitches have been reported so far including volumetric 3D printing [12][13], photoresponsive semiconductors [14][15][16][17], photopharmacology [18][19], energy storage materials [20][21][22][23], data storage materials [24], super-resolution microscopy [25

• ][26][27], photomechanical materials [28][29][30][31][32], and so on. As seen in these representative application examples, the thermal stability of the colorless and colored isomers is one of the essential properties of molecular photoswitches. For example, the photochemically reversible-type (P-type

A fiber-optic spectroscopic setup for isomerization quantum yield determination

• Anouk Volker,
• Jorn D. Steen and
• Stefano Crespi

Beilstein J. Org. Chem. 2024, 20, 1684–1692, doi:10.3762/bjoc.20.150

• actinometry, thus demonstrating the reliability of our setup. Keywords: isomerization; molecular photoswitches; photochemistry; photon flux; UV–vis spectroscopy; Introduction Photoswitches are molecules that can undergo a light-driven structural rearrangement to populate a metastable state of the initial

Cation-induced ring-opening and oxidation reaction of photoreluctant spirooxazine–quinolizinium conjugates

• Phil M. Pithan,
• Sören Steup and
• Heiko Ihmels

Beilstein J. Org. Chem. 2020, 16, 904–916, doi:10.3762/bjoc.16.82

• photoreluctant spirooxazine derivatives with regard to the electrocyclic ring opening, and they could not be employed as molecular photoswitches. At the same time, however, we discovered that the addition of Cu2+ or Fe3+ to the conjugates 3a and 3b, respectively, led to the fast and quantitative formation of

Synthesis and circularly polarized luminescence properties of BINOL-derived bisbenzofuro[2,3-b:3’,2’-e]pyridines (BBZFPys)

• Ryo Takishima,
• Yuji Nishii,
• Tomoaki Hinoue,
• Yoshitane Imai and
• Masahiro Miura

Beilstein J. Org. Chem. 2020, 16, 325–336, doi:10.3762/bjoc.16.32

• -dimensional displays [22], information storage systems [23], molecular photoswitches [24], etc. Among a series of chiral scaffolds for CPL emitting molecules, axially chiral 1,1’-bi-2-naphthol (BINOL) has been frequently adopted for the core structure owing to the availability of both enantiomers as well as

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

• yields of photoisomerization with relatively low intensity of light and minimal photobleaching even over hundreds of cycles. A third reason is the relatively high synthetic accessibility to azobenzenes. All these properties make azobenzene compounds ideal molecular photoswitches to control protein

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

• through two-photon fluorescence measurements [29]. Conclusion Hydrazones are a promising new class of molecular photoswitches. In this work we investigated the spectroscopic properties of hydrazone 1, a member of this family showing very interesting properties, such as high-isomerization quantum yield

Reversible switching of arylazopyrazole within a metal–organic cage

• Anton I. Hanopolskyi,
• Soumen De,
• Michał J. Białek,
• Yael Diskin-Posner,
• Liat Avram,
• Moran Feller and
• Rafal Klajn

Beilstein J. Org. Chem. 2019, 15, 2398–2407, doi:10.3762/bjoc.15.232

• Arylazopyrazoles represent a new family of molecular photoswitches characterized by a near-quantitative conversion between two states and long thermal half-lives of the metastable state. Here, we investigated the behavior of a model arylazopyrazole in the presence of a self-assembled cage based on Pd–imidazole

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

• the biological activity of small molecules in vitro or in vivo comprises numerous opportunities for example in the elucidation of biochemical pathways or the reduction of systemic side effects in drug therapy. Molecular photoswitches, i.e., compounds that undergo changes in their geometry and

• physicochemical properties upon irradiation with light, represent one major approach to this. One of the most common light-driven transformations exploited in molecular photoswitches is the E–Z isomerization of double bonds [18]. In this context, the photochemistry of stilbenes and the closely related azobenzenes

Precious metal-free molecular machines for solar thermal energy storage

• Meglena I. Kandinska,
• Snejana M. Kitova,
• Vladimira S. Videva,
• Stanimir S. Stoyanov,
• Stanislava B. Yordanova,
• Stanislav B. Baluschev,
• Silvia E. Angelova and
• Aleksey A. Vasilev

Beilstein J. Org. Chem. 2019, 15, 1096–1106, doi:10.3762/bjoc.15.106

• -crown-5 ether; benzothiazolium crown ether-containing styryl dyes; E/Z photoisomerization; molecular solar thermal system; Introduction Molecular photoswitches permanently attract considerable interest because they hold potential for application in molecular electronic and photonic devices [1][2][3][4

Control over molecular motion using the cis–trans photoisomerization of the azo group

• Estíbaliz Merino and
• María Ribagorda

Beilstein J. Org. Chem. 2012, 8, 1071–1090, doi:10.3762/bjoc.8.119

• between the trans and cis isomer but in turn destabilizes one of the helices of the cis isomer, and only one cis isomer (P) is present in solution (Figure 22). Conclusion Azobenzene is one of the most used systems in the design of molecular photoswitches. The synthesis is very easy and their photochromic