Deep-blue emitting 9,10-bis(perfluorobenzyl)anthracene

• Long K. San,
• Sebastian Balser,
• Brian J. Reeves,
• Tyler T. Clikeman,
• Yu-Sheng Chen,
• Steven H. Strauss and
• Olga V. Boltalina

Beilstein J. Org. Chem. 2025, 21, 515–525, doi:10.3762/bjoc.21.39

• , respectively. In this work, we explored the effects of the bulky and electron-withdrawing substituent perfluorobenzyl (BnF) on the photophysical properties and on the air- and photostability of ANTH for the first time. We hypothesized that the steric bulk of BnF and the flexibility of the –CF2– moiety between

• increasing n [22]. In this work, we report the first synthesis of ANTH(BnF)n derivatives (n = 1, 2), molecular and solid-state structures, and their photophysical properties. Results and Discussion Synthesis Perfluoroalkylation of anthracene has been previously achieved by bottom-up syntheses [23], three

• devices, can differ and this requires further studies. Photophysical properties Absorption and emission spectra of ANTH and 9,10-ANTH(BnF)2 are shown in Figure 1. The maximum λabs and λem values for ANTH and the 9,10-disubstituted ANTH derivatives are shown in Table 1. The maximum λem of 9,10-ANTH(BnF)2

Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye

• Metodej Dvoracek,
• Brendan Twamley,
• Mathias O. Senge and
• Mikhail A. Filatov

Beilstein J. Org. Chem. 2025, 21, 500–509, doi:10.3762/bjoc.21.37

• light irradiation, undergoing rearrangement and photodegradation, so there may be a risk of degradation if irradiation using UV light is tried. Alternatively, the lack of a [2 + 2] cycloaddition of Me2B, may be due to its photophysical properties not allowing for a reaction to occur, rather than the

• its photophysical properties. While a pure sample of the dimer has not yet been isolated, a UV–vis spectrum of Cl2B after 1.75 hours of irradiation in DCM was recorded. The peak corresponding to the remaining monomer was observed, along with a new peak blueshifted by 47 nm compared to the parent

• 1:1 (v/v) solution which was left to evaporate at room temperature over the course of a few days. Photophysical properties Fluorescence spectra were measured on a Horiba FluoroMax Plus spectrofluorimeter. UV–vis spectra were measured on a Shimadzu UV-1900i UV–vis spectrophotometer. Absorption and

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

• Abstract Diazocines are photoswitches derived from azobenzenes by bridging the two phenyl rings in ortho position with a CH2CH2 group forming an eight membered (diazocine) ring. Diazocine is superior to most azobenzenes in almost all photophysical properties (switching efficiency, quantum yield

• photoswitches with superior photophysical properties. The parent ethylene-bridged diazocine shows excellent switching photoconversion between the Z and the E configurations (Γ(Z → E)385nm = 92% and Γ(E → Z)520nm > 99% in n-hexane) due to well-separated n–π*-transitions in the visible part of the electromagnetic

• ). The reverse effect was observed with amino-substituted 21. The photophysical properties of photoswitchable drugs in photopharmacology are usually determined in organic solvents. Their natural environment, however, is the aqueous phase. There is a risk of overestimating the performance of photochromic

Photomechanochemistry: harnessing mechanical forces to enhance photochemical reactions

• Francesco Mele,
• Ana M. Constantin,
• Andrea Porcheddu,
• Raimondo Maggi,
• Giovanni Maestri,
• Nicola Della Ca’ and
• Luca Capaldo

Beilstein J. Org. Chem. 2025, 21, 458–472, doi:10.3762/bjoc.21.33

• light and promote mass transfer. As understanding of the methodology advances, the development of more complex synthetic strategies, including C–H, C–C, and C–heteroatom-bond formation, is expected [79]. Moreover, we anticipate that the difference in photophysical properties between organic molecules in

Unraveling aromaticity: the dual worlds of pyrazole, pyrazoline, and 3D carborane

• Zahra Noori,
• Miquel Solà,
• Clara Viñas,
• Francesc Teixidor and
• Jordi Poater

Beilstein J. Org. Chem. 2025, 21, 412–420, doi:10.3762/bjoc.21.29

• photoinduced electron transfer [8][9]. Thanks to their notable photophysical properties, pyrazoles are applied in OLED technology [10]. Noticeably, in its ground state, pyrazole (C3H4N2) is an aromatic molecule that follows Hückel's rule, with two formal double bonds and a lone pair on one nitrogen generating

Red light excitation: illuminating photocatalysis in a new spectrum

• Lucas Fortier,
• Corentin Lefebvre and
• Norbert Hoffmann

Beilstein J. Org. Chem. 2025, 21, 296–326, doi:10.3762/bjoc.21.22

• advantageous for large-scale applications, offering enhanced safety and operational simplicity. Traditionally, research in this field has focused on metal-based photocatalysts, particularly those based on transition metals like ruthenium and osmium due to their intrinsic photophysical properties. However, with

•  4d) [30]. In a continuation of this trend, a recent study by O. S. Wenger et al. further expands the frontiers of red-light photoredox catalysis with first-row transition metals by introducing Cr(0) luminophores that exhibit photophysical properties competitive with Ru(II) and Os(II) complexes [31

• that the photocatalytic efficiency of these molecules does not necessarily rely on the presence of a central metal atom. Free-base porphyrins, in particular, have demonstrated significant potential in red-light-driven transformations due to their versatile photophysical properties. These metal-free

Synthesis and characterizations of highly luminescent 5-isopropoxybenzo[rst]pentaphene

• Islam S. Marae,
• Jingyun Tan,
• Rengo Yoshioka,
• Zakaria Ziadi,
• Eugene Khaskin,
• Serhii Vasylevskyi,
• Ryota Kabe,
• Xiushang Xu and
• Akimitsu Narita

Beilstein J. Org. Chem. 2025, 21, 270–276, doi:10.3762/bjoc.21.19

• reaction conditions to selectively obtain BPP-OiPr 3 in 55% yield from dialdehyde 1. Additionally, oxidation of BPP-OiPr 3 provided BPP-dione 4 in 70% yield. The photophysical properties of BPP-OiPr 3 and BPP-dione 4 were carefully studied, examining the solvent-polarity dependence of their optical spectra

• allow more radiative transitions. On the other hand, a broad and featureless PL spectrum with the maximum at 538 nm was observed for BPP-dione 4 in toluene with a high PLQY of 0.62, which is again significantly enhanced from that of BPP 2. To gain further insight into the photophysical properties of BPP

• -0495, Japan X-ray diffraction facility, Department of Chemistry, 100 E. 24th Street, The University of Texas at Austin, Austin, TX 78712, USA 10.3762/bjoc.21.19 Abstract A benzo[rst]pentaphene (BPP) substituted by an isopropoxy group (BPP-OiPr) was synthesized in a facile manner. Its photophysical

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

• confirmed that the colorless solution of N4(o) turned yellow upon irradiation with UV light and returned to the initial color upon removal of the irradiation. The photophysical properties of N3, N4, and I1–I4 are summarized in Table 1 together with the data of N1 and N2. Thermal back reactivity in n-hexane

• experimental values. These results contribute to the design of advanced photochromic materials with tailored thermal and photophysical properties. Experimental General Commercially available reagents were used as received for the syntheses. Solvents used for spectroscopy were of spectroscopic grade or purified

• -diarylethene derivatives N1–N4 and I1–I4 investigated in this work. Synthetic route to aza-diarylethenes N4 and I1–I4. Photophysical properties and activation parameters for the thermal back reaction of compounds N1–N4 and I1–I4 in n-hexane. The differences in ΔG‡ between the theoretical value by DFT

Synthesis, characterization, and photophysical properties of novel 9‑phenyl-9-phosphafluorene oxide derivatives

• Shuxian Qiu,
• Duan Dong,
• Jiahui Li,
• Huiting Wen,
• Jinpeng Li,
• Yu Yang,
• Shengxian Zhai and
• Xingyuan Gao

Beilstein J. Org. Chem. 2024, 20, 3299–3305, doi:10.3762/bjoc.20.274

• HRMS spectrometry were in full agreement with the expected structures, and single-crystal X-ray diffraction analysis was conducted to confirm the structure of compound 7-H. Moreover, the photophysical properties of these PhFlOP derivatives were determined by UV–vis absorption and photoluminescence

• studies, revealing that their photophysical behavior can be affected by the different substituents in the donor carbazole group. Keywords: carbazole; D−A−D type; noble-metal-free system; 9‑phenyl-9-phosphafluorene oxide; photophysical properties; Introduction π-Conjugated molecular materials containing

• electrochemical studies, showing that the photophysical properties of PhFlOP depend on the nature of the electron-donating groups [31]. Later, Wu and co-workers introduced various electron donors to the PhFlOP unit to form new TADF emitters with high electroluminescence efficiency [32][33]. Despite this progress

Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade

• Merve Yence,
• Dilgam Ahmadli,
• Damla Surmeli,
• Umut Mert Karacaoğlu,
• Sujit Pal and
• Yunus Emre Türkmen

Beilstein J. Org. Chem. 2024, 20, 3290–3298, doi:10.3762/bjoc.20.273

• focus of extensive research within the past two decades due to their interesting structural features, attractive photophysical properties, and diverse applications [2]. Indeed, fluoranthenes are particularly useful in supramolecular chemistry, organic electronics, and materials science [3] as

Efficient synthesis of fluorinated triphenylenes with enhanced arene–perfluoroarene interactions in columnar mesophases

• Yang Chen,
• Jiao He,
• Hang Lin,
• Hai-Feng Wang,
• Ping Hu,
• Bi-Qin Wang,
• Ke-Qing Zhao and
• Bertrand Donnio

Beilstein J. Org. Chem. 2024, 20, 3263–3273, doi:10.3762/bjoc.20.270

• compounds, Gnm, exhibit a rectangular columnar phase (Colrec) also over large temperature ranges from ambient up to 183 and 164 °C, respectively. The unsymmetrically alkoxy-substituted derivative, G48, also displays a Colrec over a similar temperature range. The compounds’ photophysical properties have also

• . Photophysical properties: UV–vis absorption and photoluminescence UV–vis absorption and fluorescence spectra of the synthesized fluorine polycyclic aromatic hydrocarbons Fn and Gnm were measured in solution (in various solvents) and thin film and the results are summarized in Figure 6 and Table S7 in Supporting

Tunable full-color dual-state (solution and solid) emission of push–pull molecules containing the 1-pyrindane moiety

• Anastasia I. Ershova,
• Sergey V. Fedoseev,
• Konstantin V. Lipin,
• Mikhail Yu. Ievlev,
• Oleg E. Nasakin and
• Oleg V. Ershov

Beilstein J. Org. Chem. 2024, 20, 3016–3025, doi:10.3762/bjoc.20.251

• 1i and 1iH+ in acidic solution. Solvatochromic properties of compound 1i. Photophysical properties of stilbazoles 1 in toluene. Photophysical properties of stilbazoles 1 in DMSO. Solid-state photoluminescence of stilbazoles 1. Supporting Information Supporting Information File 2: Synthetic procedure

Synthesis of benzo[f]quinazoline-1,3(2H,4H)-diones

• Ruben Manuel Figueira de Abreu,
• Peter Ehlers and
• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 2708–2719, doi:10.3762/bjoc.20.228

• other compounds with medicinal or photophysical properties [52][53][54][55]. Compounds A are related to the class of natural products known as coumestans, while B resembles flavins. While the medical potential of coumestans is still the subject of current research, interesting photocatalytic properties

• properties All synthesized compounds exhibit photoluminescence by excitation with UV light. Hence, we studied the photophysical properties of all obtained derivatives 5 by steady-state absorption and fluorescence spectroscopy. The influence of the substitution pattern on the photophysical properties is

• various functional groups. The optical properties of as-prepared derivatives were investigated by steady-state absorption and photoluminescence spectroscopy. The photophysical properties are strongly altered by the presence N,N-dimethylaniline functional groups on the scaffold, which leads to strongly

Photoluminescence color-tuning with polymer-dispersed fluorescent films containing two fluorinated diphenylacetylene-type fluorophores

• Kazuki Kobayashi,
• Shigeyuki Yamada,
• Motohiro Yasui and
• Tsutomu Konno

Beilstein J. Org. Chem. 2024, 20, 2682–2690, doi:10.3762/bjoc.20.225

• 10 s. For photophysical measurements, thin and smooth films were prepared by spin-coating followed by solvent evaporation. Photophysical properties The PL spectra and quantum yields were measured using a Quantaurus-QY C11347-01 absolute PL quantum yield spectrometer (Hamamatsu Photonics, Japan). The

Novel truxene-based dipyrromethanes (DPMs): synthesis, spectroscopic characterization and photophysical properties

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2024, 20, 2163–2170, doi:10.3762/bjoc.20.186

• in addition to the stimulating photophysical properties and distinct architectures emerging from the self-assembly processes [42]. Noticeably, most extensively used DPMs belong to the 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY), owing to their high propensity toward chemical manipulations and

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

• Ignaz Betcke,
• Alissa C. Götzinger,
• Maryna M. Kornet and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

• agrochemical uses of pyrazoles [13] include insecticides [14], herbicides [15], and fungicides [16]. Furthermore, they are widely applied for the assembly of supramolecular ensembles [17] and molecular systems capable of photoinduced electron transfer [18]. Due to their pertinent photophysical properties [19

A new platform for the synthesis of diketopyrrolopyrrole derivatives via nucleophilic aromatic substitution reactions

• Vitor A. S. Almodovar and
• Augusto C. Tomé

Beilstein J. Org. Chem. 2024, 20, 1933–1939, doi:10.3762/bjoc.20.169

• region [3][4]. In turn, N-substituted DPP derivatives are soluble in common organic solvents, exhibit large molar extinction coefficients, Stokes shifts in the range of 10–70 nm and high fluorescence quantum yields [5][6][7]. Due to their outstanding photophysical properties, DPP-based dyes have been

• consistently displayed the protonated molecular ion [M + H]+ as the base peak. The UV–vis and fluorescence spectra of DPP derivatives 3a–f, 4a, 4d and 4f in DMF are presented in Figure 1, and their photophysical properties are summarized in Table 1. These compounds are highly fluorescent, and their UV–vis

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

• Cristina Martini,
• Muhammad Idham Darussalam Mardjan and
• Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

• on biological activities or photophysical properties (i.e., fluorescence) of GBB adducts. Another advantage is that, by replacing the amidine component (classically 2-aminopyridines) with other heterocycles, different scaffolds are obtained, and this is extremely efficient in diversity-oriented

• generation of new scaffolds by coupling the GBB reaction with other transformations; d) the study of the biological and pharmacological properties of these fused heterocycles; e) the study of the photophysical properties of the GBB adducts. At the end of this overview, conclusions will be drawn about the

A facile three-component route to powerful 5-aryldeazaalloxazine photocatalysts

• Ivana Weisheitelová,
• Radek Cibulka,
• Marek Sikorski and
• Tetiana Pavlovska

Beilstein J. Org. Chem. 2024, 20, 1831–1838, doi:10.3762/bjoc.20.161

• artificial systems. Additionally, 5-deazaflavins have emerged as prospective antitumor agents [9][10]. Surprisingly, among the broad family of flavin derivatives, 5-deazaalloxazines have received less attention regarding their photophysical properties, despite their close similarity to the above-mentioned 5

• of photocatalysts by tuning their redox and photophysical properties. Thus, we successfully developed a one-pot, three-component synthetic method with those substituents in 5-aryldeazaflavins 1 on the deazaisoalloxazine core or on the phenyl ring by condensation of N-substituted anilines, aromatic

• methyl substituents were chosen to enhance the photophysical properties and photostability of the desired photocatalysts. It should be noted that our method encountered limitations when applying strongly deactivated anilines substituted with CF3 or acetyl groups, with no formation of 5

Photoswitchable glycoligands targeting Pseudomonas aeruginosa LecA

• Yu Fan,
• Ahmed El Rhaz,
• Stéphane Maisonneuve,
• Emilie Gillon,
• Maha Fatthalla,
• Franck Le Bideau,
• Guillaume Laurent,
• Samir Messaoudi,
• Anne Imberty and
• Juan Xie

Beilstein J. Org. Chem. 2024, 20, 1486–1496, doi:10.3762/bjoc.20.132

• possess excellent photophysical properties and strong affinity for targeted LecA with Kd values in the micromolar range. Analysis of the thermodynamic contribution indicates that the Z-azobenzene isomers have a systematically stronger favorable enthalpy contribution than the corresponding E-isomers, but

•  1). All the photophysical properties of compounds 1–5 are summarized in Table 1 (spectra are shown in Figure S1–S24 in Supporting Information File 1). Concerning the meta-substituted azobenzene 2, a 30 nm blue shift is observed for the π→π* transition (λmax = 321 nm) as well as a lower absorption

Synthesis and optical properties of bis- and tris-alkynyl-2-trifluoromethylquinolines

• Stefan Jopp,
• Franziska Spruner von Mertz,
• Peter Ehlers,
• Alexander Villinger and
• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 1246–1255, doi:10.3762/bjoc.20.107

• and applied to palladium-catalysed Sonogashira reactions. Optimised reaction conditions allow the synthesis of various bis- or tris-alkynylated products in one step. Products were generally obtained in high yields and intensive fluorescence. The photophysical properties of selected compounds were

Mechanistic investigations of polyaza[7]helicene in photoredox and energy transfer catalysis

• Johannes Rocker,
• Till J. B. Zähringer,
• Matthias Schmitz,
• Till Opatz and
• Christoph Kerzig

Beilstein J. Org. Chem. 2024, 20, 1236–1245, doi:10.3762/bjoc.20.106

• photocatalyst (PC•+/PC = +1.12 V vs SCE) is then regenerated by an electron transfer from sodium p-toluenesulfinate (TsNa) (Ts•/Ts− = +0.70 V vs SCE) closing the photocatalytic cycle [45]. Unlike other prominent photocatalysts, little to nothing is known about the reactivity, the photophysical properties or the

Introduction of peripheral nitrogen atoms to cyclo-meta-phenylenes

• Koki Ikemoto and
• Hiroyuki Isobe

Beilstein J. Org. Chem. 2024, 20, 1207–1212, doi:10.3762/bjoc.20.103

• achieved with one-pot Suzuki–Miyaura coupling to arrange phenylene rings and pyridinylene rings in an alternating fashion. Analyses with UV–vis spectroscopy showed changes in the photophysical properties with nitrogen doping, and X-ray crystallographic analyses experimentally revealed the presence of

• dopants. Photophysical properties of 3a and 3b. (a) UV–vis spectrum of 3a in CHCl3. (b) UV–vis spectrum of 3b in CHCl3. For reference, the spectra of [6]CMP and [8]CMP from the literature are also shown in gray [15]. Crystal structures of 3a and 3b. (a) Molecular structures. Biaryl dihedral angles (ω) are

Novel route to enhance the thermo-optical performance of bicyclic diene photoswitches for solar thermal batteries

• Akanksha Ashok Sangolkar,
• Rama Krishna Kadiyam and
• Ravinder Pawar

Beilstein J. Org. Chem. 2024, 20, 1053–1068, doi:10.3762/bjoc.20.93

• we report our attempt to enhance both the thermochemical and photophysical properties in a single-bridged bicyclic diene (BBD)-based photoswitch by elongating the unsaturated bridge with different heteroatomic units. To elucidate the best elongation unit, the energy storage capacity and the TBR

• barriers were accounted using the DLPNO-CCSD(T) and (8,8)-CASPT2 methods, respectively. The photophysical properties including the absorption onset, excitation wavelengths, and the absorption intensities were extensively investigated with the time-dependent calculations. The result provides information on

• , the improvement of both the thermochemical and photophysical properties of a photoswitching couple is a challenging task. The bicyclooctadiene/tetracyclooctane (BOD/TCO) couple structurally resembles the NBD/QC pair but has an extended saturated bridge due to the additional methylene (-CH2-) unit. An

Synthesis and properties of 6-alkynyl-5-aryluracils

• Ruben Manuel Figueira de Abreu,
• Till Brockmann,
• Alexander Villinger,
• Peter Ehlers and
• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 898–911, doi:10.3762/bjoc.20.80

• synthesized by other methods and the single Suzuki reaction on uracil is well studied [42][69][70][71]. Physical properties The photophysical properties of selected derivatives were investigated by steady-state absorption and photoluminescence spectroscopy. The influence of the substitution pattern on the

• photophysical properties is displayed in Figure 4. Corresponding photophysical data and quantum yields are described in Table 2. The analysis of the absorption spectra revealed that the spectra can be divided into a short-wave and long-wave region. In the long wavelength region (350–500 nm) all measured

• gives first insights into the optical properties. It was observed that the photophysical properties could be partially modulated by the chosen substituents. Experimental General information Nuclear magnetic resonance spectra (1H/13C/19F NMR) were recorded on a Bruker AVANCE 300 III, 250II, or 500. The