Metal-free double azide addition to strained alkynes of an octadehydrodibenzo[12]annulene derivative with electron-withdrawing substituents

• Naoki Takeda,
• Shuichi Akasaka,
• Susumu Kawauchi and
• Tsuyoshi Michinobu

Beilstein J. Org. Chem. 2024, 20, 2234–2241, doi:10.3762/bjoc.20.191

• ] cycloaddition–retroelectrocyclization (CA-RE) between electron-rich alkynes and electron-deficient olefins [8]. The [2 + 2] CA-RE click reactions were employed to produce a variety of functional materials, such as nonlinear optical chromophores [9][10], super acceptors [11][12], ion sensing D–A systems [13

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

• ), organogels, molecular wires, self-assembly and so forth [14][15][16][17][18][19][20][21][22][23][24][25]. Moreover, nowadays these invaluable compounds have also received great attention of supramolecular chemists, and finds applications in sensing, catalysis, donor–acceptor systems, energy transfer and

• the importance of DPMs in mind due to their utmost significance as a building block in the construction of porphyrinogens, related polypyrrolic macrocycles, and pigments [39][40][41]. As shown in Figure 1, these DPMs and many more have fruitfully been used by several research groups in sensing/binding

• outstanding optical properties [43]. Herein, we present for the first time three new mono-, di-, tri-dipyrromethane appended truxene derivatives with the intention to explore them for future sensing and/or binding properties. Results and Discussion To achieve our goal towards the construction of truxene

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

• increasingly limited for treatment of infections. PA has been classified as a priority 1 pathogen by the WHO [2][3]. Various approaches to treating PA, in addition to traditional antibiotics, have been developed including inhibition of quorum sensing, biofilm formation, iron chelation, and interfering with

Stability trends in carbocation intermediates stemming from germacrene A and hedycaryol

• Naziha Tarannam,
• Prashant Kumar Gupta,
• Shani Zev and
• Dan Thomas Major

Beilstein J. Org. Chem. 2024, 20, 1189–1197, doi:10.3762/bjoc.20.101

• several significant processes, terpenoids play an indispensable role in cell-wall and membrane biosynthesis, sensing, plant defense, electron transport, or conversion of light into chemical energy [1][2]. Based on the number of hydrocarbon units, terpenes are classified into various families like

A Diels–Alder probe for discovery of natural products containing furan moieties

• Alyssa S. Eggly,
• Namuunzul Otgontseren,
• Carson B. Roberts,
• Amir Y. Alwali,
• Haylie E. Hennigan and
• Elizabeth I. Parkinson

Beilstein J. Org. Chem. 2024, 20, 1001–1010, doi:10.3762/bjoc.20.88

• the titers of MMFs in native producing strains. However, if titers are similar to that of γ-butyrolactones and butenolides quorum sensing molecules, we would expect them to be between 80 and 2.5 nM [29][30][31]. Given these very low concentrations, cultures would need to be greatly concentrated (≈1000

Activity assays of NnlA homologs suggest the natural product N-nitroglycine is degraded by diverse bacteria

• Kara A. Strickland,
• Brenda Martinez Rodriguez,
• Ashley A. Holland,
• Shelby Wagner,
• Michelle Luna-Alva,
• David E. Graham and
• Jonathan D. Caranto

Beilstein J. Org. Chem. 2024, 20, 830–840, doi:10.3762/bjoc.20.75

• ), limiting the use of this model to predict the heme environment. Nevertheless, this protein–ligand model heme binding between the β-sheet and an α-helix based on similarity to the oxygen-sensing dimeric DosH protein [34]. DosH is also a heme-binding PAS-domain containing protein, further validating the

Methodology for awakening the potential secondary metabolic capacity in actinomycetes

• Shun Saito and
• Midori A. Arai

Beilstein J. Org. Chem. 2024, 20, 753–766, doi:10.3762/bjoc.20.69

• ), which upon sensing ROS, release their repression and activate the expression of various genes [93][94][95]. Wei et al. reported that the production of validamycin A (25) by Streptomyces hygroscopicus 5008 could be activated at the transcriptional level by simply adding hydrogen peroxide (H2O2; which

Possible bi-stable structures of pyrenebutanoic acid-linked protein molecules adsorbed on graphene: theoretical study

• Yasuhiro Oishi,
• Motoharu Kitatani and
• Koichi Kusakabe

Beilstein J. Org. Chem. 2024, 20, 570–577, doi:10.3762/bjoc.20.49

• can be expected for proteins immobilized on graphene. As a result, we propose a strategy for improving the accuracy of the sensing process in elastic wave measurement sensors through antigen/antibody reactions. Results and Discussion PASE and PASE-derivatives on graphene Among pyrene derivatives, PASE

• conformation 2 in the protein capture step. On the other hand, at the time of sensing, the proteins and sample antigens bound by the linker should be strongly bound on the graphene surface. This makes it easier to observe the increased mass by generating a reflected wave with a strong amplitude relative to the

• other hand, in non-covalent functionalization, the electronic properties of graphene can be preserved [27][28][29]. Therefore, the PASE linker and its properties may be relevant for another type of the electronic sensing strategy, such as field effect transistor-based biosensors. Conclusion We discussed

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

• represents prototypes of molecular machines in which guest binding is regulated by stimuli-induced conformational changes between open and closed states (Figure 1). This feature holds significant promise for applications in sensing, drug delivery, or membrane transport within biological systems. Moreover

Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

• Aissam Okba,
• Pablo Simón Marqués,
• Kyohei Matsuo,
• Naoki Aratani,
• Hiroko Yamada,
• Gwénaël Rapenne and
• Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

• dithienonaphthalene products (e.g., 16) exhibit very different fluorescence properties, S-extrusion from thiophene-annelated thiepines was consequently exploited for peroxide sensing. Very recently, Zhou et al. reported the synthesis of S-doped phenanthrene and triphenylene derivatives via the thermally-induced ring

• dithienonaphthalenes, upon S-extrusion triggered by electrochemical oxidation. Bottom: Exploitation of the S-extrusion process for peroxide sensing, taking advantage of the lability of oxidized dithienobenzothiepine to generate highly fluorescent dithienonaphthalene [63]. Synthesis of S-doped extended triphenylene

Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors

• Yordanka Mollova-Sapundzhieva,
• Plamen Angelov,
• Danail Georgiev and
• Pavel Yanev

Beilstein J. Org. Chem. 2023, 19, 1804–1810, doi:10.3762/bjoc.19.132

• sensing; Introduction Among the vast number of biologically active quinoline derivatives [1][2], the subclass of 4-quinolones (also referred to as 4-oxo-1,4-dihydroquinolines, quinolin-4(1H)-ones, or 4-hydroxyquinolines) is of great importance with its rich variety of bioactive compounds. Perhaps the

• great research interest, with many reviews published in the recent years [20][21][22]. Some of the compounds are known to act as antibiotics [23][24][25][26], while others function as quorum-sensing signal molecules which regulate the production and release of virulence factors in bacteria, thus helping

• conditions, and allows easy installation of long-chain substituents at the C-2 position of the quinolone core. These characteristics of the synthetic method could be particularly attractive in the search of novel mimics of the Pseudomonas quorum-sensing signal molecules. The high activity of compounds 4d and

Trifluoromethylated hydrazones and acylhydrazones as potent nitrogen-containing fluorinated building blocks

• Zhang Dongxu

Beilstein J. Org. Chem. 2023, 19, 1741–1754, doi:10.3762/bjoc.19.127

• pharmacological activities [86][87]. Acylhydrazones can exist in either E or Z forms in solution, and they can exhibit good optical properties for applications as photoswitches, in luminescence sensing, and as metallo-assemblies [88][89]. In organic synthesis, acylhydrazones have served as stable imine

Quinoxaline derivatives as attractive electron-transporting materials

• Zeeshan Abid,
• Liaqat Ali,
• Sughra Gulzar,
• Faiza Wahad,
• Raja Shahid Ashraf and
• Christian B. Nielsen

Beilstein J. Org. Chem. 2023, 19, 1694–1712, doi:10.3762/bjoc.19.124

• -emitting diodes (OLEDs), and bio/chemo-sensing devices. The movement of charge carriers through these materials occurs via a complex interplay of electronic, structural, and energetic phenomena, presenting intriguing challenges and opportunities for scientific exploration [3][4]. Quinoxalines (Qxs) have

• , environmental monitoring, and chemical sensing. Additionally, they can be utilized for biosensing applications by leveraging their ability to absorb and emit light in the near-infrared II range. This range allows for deeper tissue penetration, reduced scattering, and minimized autofluorescence, thereby enabling

Tying a knot between crown ethers and porphyrins

• Maksym Matviyishyn and
• Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

• synthesis of three-dimensional cryptands by Lehn [5], and spherands by Cram [6]. Later on, various classes of macrocyclic compounds were designed, demonstrating remarkable features in areas spreading from simple coordination chemistry [7], through host–guest chemistry, sensing [8], biomedicine [9], and

• . Osuka and co-workers provided novel insight into the meso-appended crown ether porphyrins, namely, chromophore-incorporated and polymer-based systems capable of acting as multitopic receptors for transition, alkali, and alkali-earth metal cations, which were proved as optical sensing agents among other

• axially bound H2O. The water molecule was stabilised by hydrogen bonding to the diaza-crown-6 core. Over the years, significant advancements have been made in crown ether-capped porphyrins, demonstrating their versatile applications in host–guest chemistry, multitopic receptor design, and cation sensing

Complexes of resorcin[4]arene with secondary amines: synthesis, solvent influence on “in-out” structure, and theoretical calculations of non-covalent interactions

• Waldemar Iwanek

Beilstein J. Org. Chem. 2023, 19, 1525–1536, doi:10.3762/bjoc.19.109

• affinity and selectivity towards specific amines. In addition to their potential applications in sensing and molecular recognition, R[4]A have also been studied for their potential pharmaceutical [13] and biochemical [14] applications. R[4]A typically exhibit complex structures containing over a hundred

Intermediates and shunt products of massiliachelin biosynthesis in Massilia sp. NR 4-1

• Till Steinmetz,
• Blaise Kimbadi Lombe and
• Markus Nett

Beilstein J. Org. Chem. 2023, 19, 909–917, doi:10.3762/bjoc.19.69

• ]. Natural products that are structurally related to 1–6 were discovered in Pseudomonas aeruginosa. It was shown that these compounds function as signaling molecules involved in quorum sensing and stress response [24] which might be an explanation for their low bioactivity against the tested bacteria. Upon

pH-Responsive fluorescent supramolecular nanoparticles based on tetraphenylethylene-labelled chitosan and a six-fold carboxylated tribenzotriquinacene

• Nan Yang,
• Yi-Yan Zhu,
• Wei-Xiu Lin,
• Yi-Long Lu and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2023, 19, 635–645, doi:10.3762/bjoc.19.45

• extensive attention owing to their potential applications in biomedicine, chemical sensing and as catalysts [1][2]. It is possible to regulate the formation and breakdown of supramolecular structures using external stimuli, such as pH, light, temperature, enzymes, and competing reagents [3][4]. Among these

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

• Dileep Kumar Singh

Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29

• microwave irradiation conditions. The prepared nanoparticles from free-base PPCs showed colorimetric aqueous pH sensing, which suggests that the PPC nanoparticles could serve as chemical sensing applications. In 2008, the Crossley’s group [59] reported the synthesis of a ‘capped’ porphyrin 142 forming a

• reaction conditions and gives higher yields of product than directly linked azido or alkynyl porphyrins. Many applications for porphyrin click products have been proposed, including chemical sensing, anion-binding affinity, photovoltaics devices, light-harvesting materials, and in the synthesis of water

Using UHPLC–MS profiling for the discovery of new sponge-derived metabolites and anthelmintic screening of the NatureBank bromotyrosine library

• Sasha Hayes,
• Aya C. Taki,
• Kah Yean Lum,
• Joseph J. Byrne,
• Merrick G. Ekins,
• Robin B. Gasser and
• Rohan A. Davis

Beilstein J. Org. Chem. 2022, 18, 1544–1552, doi:10.3762/bjoc.18.164

• the purealidin bromotyrosine structure class, however, quorum sensing inhibition and antifouling activities against several strains of bacteria and microalgae appears in the literature [33][34], while HIV-1 replication inhibition and anti-Leishmania and Plasmodium activity has also been recorded [35

1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host–guest complexes

• Artem N. Semakin,
• Ivan S. Golovanov,
• Yulia V. Nelyubina and
• Alexey Yu. Sukhorukov

Beilstein J. Org. Chem. 2022, 18, 1424–1434, doi:10.3762/bjoc.18.148

• stabilization of the complex through weak hydrophobic interactions of with tert-butyl groups of Boc. We believe that by adjustment of the substituents on the amide/carbamate groups, receptors for supramolecular sensing of alcohols [44] could be designed based on 3N-TAADs of type 4. Further research in this

Thermally activated delayed fluorescence (TADF) emitters: sensing and boosting spin-flipping by aggregation

• Ashish Kumar Mazumdar,
• Gyana Prakash Nanda,
• Nisha Yadav,
• Upasana Deori,
• Upasha Acharyya,
• Bahadur Sk and
• Pachaiyappan Rajamalli

Beilstein J. Org. Chem. 2022, 18, 1177–1187, doi:10.3762/bjoc.18.122

• thermally activated delayed fluorescence (TADF) characteristics are emerging due to the potential applications in optoelectronic devices, time-resolved luminescence imaging, and solid-phase sensing. Herein, we synthesized two (4-bromobenzoyl)pyridine (BPy)-based donor–acceptor (D–A) compounds with varying

• as well as the relevance for fluorescence-based acid–base sensing. Keywords: intramolecular charge transfer; molecular aggregates; sensing; thermally activated delayed fluorescence (TADF); Introduction Metal-free organic solid-state emitters have gained increasing interest in recent years due to

• the potential applications in optoelectronic devices [1][2][3][4], solid-phase sensing [5], bioimaging [6][7], security [8], and storage devices [9]. The optical and electrochemical properties of the organic emitters can be tuned by external stimuli, such as mechanical force, heat, solvent, acid and

Post-synthesis from Lewis acid–base interaction: an alternative way to generate light and harvest triplet excitons

• Hengjia Liu and
• Guohua Xie

Beilstein J. Org. Chem. 2022, 18, 825–836, doi:10.3762/bjoc.18.83

• intermolecular mechanism, considered as post-synthesis of new luminescent compounds offers promising applications in sensing and electroluminescence by manipulating the frontier molecular orbital energy levels of organic conjugated materials, simply based on Lewis acid–base chemistry. Keywords: excitons

• ][32], e.g., organic thin-film transistors [45][46], organic photovoltaics [47], and chemical sensing [48]. Chemical structures of Lewis acid examples. Chemical structures of Lewis basic fluorescent polymer poly{2,5-pyridylene-co-1,4-[2,5-bis(2-ethylhexyloxy)]phenylene} 1 and D–A–D compound 2,5-bis((N

Heteroleptic metallosupramolecular aggregates/complexation for supramolecular catalysis

• Prodip Howlader and
• Michael Schmittel

Beilstein J. Org. Chem. 2022, 18, 597–630, doi:10.3762/bjoc.18.62

• have led to a multitude of extremely useful functional applications (molecular recognition, ion sensing, catalysis, etc.) [9][22]. Since most of these structures are homoleptic in nature, i.e., they are constructed from a single type of ligand [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19

BINOL as a chiral element in mechanically interlocked molecules

• Matthias Krajnc and
• Jochen Niemeyer

Beilstein J. Org. Chem. 2022, 18, 508–523, doi:10.3762/bjoc.18.53

• topic is divided into three subcategories, namely (mechano)intramolecular chirality transfer (section 2.1), stereoselective catalysis (section 2.2), and stereoselective sensing (section 2.3). Finally, we give a short conclusion about BINOL as a chiral element in interlocked molecules. Review 1

• slightly higher barrier, which is probably the reason for the low overall stereoselectivities. 2.3 Stereoselective sensing As last part of this minireview, we will present the application of BINOL-based interlocked molecules for stereoselective chemosensing. This research field was pioneered by Beer and co

• to slightly better stereodiscrimation of the guest molecules (see Figure 17). Subsequently, Beer and co-workers reported the first example of a chiral halogen-bonding [3]rotaxane for the recognition and sensing of dicarboxylate anions [64]. The [3]rotaxane (S)-68 was prepared in a two-fold clipping

Synthesis of a novel aminobenzene-containing hemicucurbituril and its fluorescence spectral properties with ions

• Qingkai Zeng,
• Qiumeng Long,
• Jihong Lu,
• Li Wang,
• Yuting You,
• Xiaoting Yuan,
• Qianjun Zhang,
• Qingmei Ge,
• Hang Cong and
• Mao Liu

Beilstein J. Org. Chem. 2021, 17, 2840–2847, doi:10.3762/bjoc.17.195

• ions at submicromolar concentrations always by means of NMR spectroscopy [33]. Nevertheless, sensing by UV–vis or fluorescence spectra was hard to realize, for there is no chromophore in the frameworks. While hemicucurbit[n]urils with improvement in solubility, they still remain poor in derivatization