Investigation of a bimetallic terbium(III)/copper(II) chemosensor for the detection of aqueous hydrogen sulfide

• Parvathy Mini,
• Michael R. Grace,
• Genevieve H. Dennison and
• Kellie L. Tuck

Beilstein J. Org. Chem. 2024, 20, 2818–2826, doi:10.3762/bjoc.20.237

• /bjoc.20.237 Abstract The chemosensor properties of a bimetallic terbium(III)/copper(II) complex functionalized with a 4-(2-pyridyl)-1,2,3-triazole ligand for the detection of Cu2+ ions and, aqueous and gaseous hydrogen sulfide was investigated. The 4-(2-pyridyl)-1,2,3-triazole ligand functions both as

• an antenna chromophore and a receptor for Cu2+ ions; the Cu2+ complex was shown to be a chemosensor for the detection of aqueous hydrogen sulfide. The chemosensor exhibited significant reversibility over multiple cycles, observed with the sequential addition of Na2S followed by Cu2+ ions. The limit

• : chemosensor; hydrogen sulfide; lanthanide; luminescence; terbium; Introduction The field of luminescent lanthanide chemosensors is rapidly evolving, driven by the need for more efficient, sensitive, and versatile detection methods for environmentally and biologically relevant analytes. While significant

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

• produced the desired amidobenzene-containing hemicucurbituril. As an original fluorescent chemosensor, it exhibited strong interactions with Fe3+ over other metal cations. The experimental evidence of fluorescence spectra suggested that a 1:1 complex was formed between this macrocycle and Fe3+ with an

Free-radical cyclization approach to polyheterocycles containing pyrrole and pyridine rings

• Ivan P. Mosiagin,
• Olesya A. Tomashenko,
• Dar’ya V. Spiridonova,
• Mikhail S. Novikov,
• Sergey P. Tunik and
• Alexander F. Khlebnikov

Beilstein J. Org. Chem. 2021, 17, 1490–1498, doi:10.3762/bjoc.17.105

• heteroaromatics available for various applications. Fused polyheteroarenes, containing a pyrrole moiety, are widely present in natural products and pharmacologically important agents and have a significant importance in the development of new materials useful for bioimaging applications and chemosensor systems [3

Optical detection of di- and triphosphate anions with mixed monolayer-protected gold nanoparticles containing zinc(II)–dipicolylamine complexes

• Lena Reinke,
• Julia Bartl,
• Marcus Koch and
• Stefan Kubik

Beilstein J. Org. Chem. 2020, 16, 2687–2700, doi:10.3762/bjoc.16.219

• introducing a method to assess whether certain biologically relevant anions are present in an aqueous solution within a specific concentration range. Keywords: chemosensor; diphosphate; gold nanoparticles; optical sensing; triphosphate; Introduction Gold nanoparticles (AuNPs) are versatile platforms for the

Et₃N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties

• Dharmender Singh,
• Vipin Kumar and
• Virender Singh

Beilstein J. Org. Chem. 2020, 16, 1740–1753, doi:10.3762/bjoc.16.146

• , β-carbolines are also used as fluorescence standards. Recently, a novel β-carboline-based fluorescent chemosensor was developed by Batra and co-workers for the quantitative analysis of fluoride ions (F−) at ppb level [19]. Sulfur-containing organic compounds are broadly associated with numerous

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

• formation of the respective oxidation product caused the development of a broad absorption band between 425 nm and 500 nm and a new emission band at λfl = 628 nm, so that it may be employed as a selective chemosensor or chemodosimeter for the colorimetric and fluorimetric detection of Cu2+ and Fe3

• cations also caused a fluorimetric response due to the developing orange emission at λfl = 628 nm so that 3a may be employed as a selective chemosensor or chemodosimeter for the colorimetric and fluorimetric detection of Cu2+ and Fe3+, respectively. As shown by NMR spectroscopic and mass spectrometric

Preparation of anthracene-based tetraperimidine hexafluorophosphate and selective recognition of chromium(III) ions

• Qing-Xiang Liu,
• Feng Yang,
• Zhi-Xiang Zhao,
• Shao-Cong Yu and
• Yue Ding

Beilstein J. Org. Chem. 2019, 15, 2847–2855, doi:10.3762/bjoc.15.278

• 10-positions of anthracene. In addition, compound 3 was used as a chemosensor to research the ability to recognize Cr3+ through fluorescence and UV titrations, HRMS, as well as 1H NMR and IR spectroscopy. The results indicate that 3 is an effective chemosensor for Cr3+. Keywords: chemosensor

• X-ray analysis as well as 1H and 13C NMR spectroscopy. Particularly, compound 3 was tested as a chemosensor for the recognition of Cr3+ through fluorescence, UV, IR, and 1H NMR spectroscopy along with HRMS. Altogether, the results indicate the utility of 3 as an effective chemosensor for Cr3

• to be a highly sensitive and selective chemosensor for Cr3+, and it can effectively distinguish Cr3+ from other cations through fluorescence enhancement. Thus, complex 3 may have potential value for the application as a Cr3+ detector. Experimental Materials and instruments The solvents and chemicals

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

• 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

• , as elucidated by the crystallographic structure of a 1:1 host–guest BAPTA system [2]. This moiety has been exploited in the development of various fluorescent supramolecular chemosensor systems and even molecular logic systems [3][4][5][6][7][8][9][10][11]. Equally, the incorporation of

Complexation of a guanidinium-modified calixarene with diverse dyes and investigation of the corresponding photophysical response

• Yu-Ying Wang,
• Yong Kong,
• Zhe Zheng,
• Wen-Chao Geng,
• Zi-Yi Zhao,
• Hongwei Sun and
• Dong-Sheng Guo

Beilstein J. Org. Chem. 2019, 15, 1394–1406, doi:10.3762/bjoc.15.139

• use and high sensitivity, and has been widely used in fields of chemistry, biomedicine, environment, and so on [1]. Generally, the conversion of a luminescent dye to a chemosensor requires a grafting recognition motif for a particular analyte, whose installation often involves laborious and time

An uracil-linked hydroxyflavone probe for the recognition of ATP

• Márton Bojtár,
• Péter Zoltán Janzsó-Berend,
• Dávid Mester,
• Dóra Hessz,
• Mihály Kállay,
• Miklós Kubinyi and
• István Bitter

Beilstein J. Org. Chem. 2018, 14, 747–755, doi:10.3762/bjoc.14.63

• ], metal-complexes [21][22][23][24][25][26][27] and other direct sensing systems [28][29][30] have significant advantages over the classical, separation-based methods. The primary difficulties in the design of an ATP chemosensor are the structural similarity of ATP to other nucleotides (i.e., to guanosine

• -5’-triphosphate, GTP) and the strong solvation of the chemosensor and the analyte in aqueous media, reducing the association constant of their complex, and through that the sensitivity of the sensor [31][32]. The molecular recognition of nucleotides in most chemosensors is achieved by charged

• way to enhance the selectivity. Since ATP has one adenine nucleobase, a simple uracil/thymine unit appended to a neutral chemosensor operating mainly through π-interaction could be a good model for investigation. We selected DMHF as the fluorophore and core scaffold because of its easy synthesis and

Phosphonic acid: preparation and applications

• Charlotte M. Sevrain,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2017, 13, 2186–2213, doi:10.3762/bjoc.13.219

• chemosensor for trinitrotoluene (TNT) [63]. The third important feature of phosphonic acid arises from its coordination properties. Indeed, the three oxygen atoms can be engaged in coordination or iono-covalent bonds. These coordination properties were used to design molecular hybrid materials [64] also

The chemistry and biology of mycolactones

• Matthias Gehringer and
• Karl-Heinz Altmann

Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159

• derivatization of mycolactone A/B (1a,b) with a 2-naphthylboronate-based fluorogenic chemosensor (Figure 4). The latter complexes the 1,3-diol moiety proximal to the pentaene motif of the lower side chain, thus resulting in enhanced fluorescence emission intensity of the mycolactone band upon irradiation with

Amidofluorene-appended lower rim 1,3-diconjugate of calix[4]arene: synthesis, characterization and highly selective sensor for Cu²⁺

• Rahman Hosseinzadeh,
• Mohammad Nemati,
• Reza Zadmard and
• Maryam Mohadjerani

Beilstein J. Org. Chem. 2016, 12, 1749–1757, doi:10.3762/bjoc.12.163

• Basic Science, University of Mazandaran, Babolsar, Iran 10.3762/bjoc.12.163 Abstract Functionalization of calix[4]arene with amidofluorene moieties at the lower rim led to formation of the 1,3-diconjugate of calix[4]arene L as a novel fluorescent chemosensor for Cu2+. The receptor molecule L exhibited

• of 9.6 × 10−8 M. Keywords: calix[4]arene; chemosensor; copper ions; fluorene; fluorescence; Introduction Owing to the substantial role of fluorescent chemosensors in biological, environmental, and chemical processes, their design and synthesis, especially for detection of metal ions has attracted

• indicates that the L binds copper as Cu2+. Fluorescence titrations of L with metal ions Fluorescence spectroscopy was applied to investigate the recognition properties of chemosensor L toward various metal ions in MeCN. In the absence of metal ions, the receptor L represents fluorescence emission at ≈365 nm

A simple and efficient dual optical signaling chemodosimeter for toxic Hg(II)

• Sabir H. Mashraqui,
• Sapna A. Tripathi,
• Sushil S. Ghorpade and
• Smita R. Britto

Beilstein J. Org. Chem. 2012, 8, 1352–1357, doi:10.3762/bjoc.8.155

• no significant interferences even in excess concentrations. Keywords: chemidosimeter; chemosensor; fluorescence; Hg(II) selective; UV–visible; visual detection; Introduction Interest continues unabatedly to design optical probes for the selective detection of metal ions of importance across

Ratiometric fluorescent probe for enantioselective detection of D-cysteine in aqueous solution

• Xiao-bo Zhou,
• Wing-Hong Chan,
• Albert W. M. Lee and
• Chi-Chung Yeung

Beilstein J. Org. Chem. 2011, 7, 1508–1515, doi:10.3762/bjoc.7.176

• enantioselective detection of cysteine in 99:1 buffered HEPES:ACN solutions. Under the measuring conditions, the sensor demonstrates high selectivity toward Cys against Hcy and GSH, and an enantioselectivity of 3.35 can be achieved for antipodal forms of Cys. Keywords: chemosensor; D-cysteine; enantioselectivity

• task to design probes for the detection of Cys. In addition, to our knowledge, an enantioselective fluorescent chemosensor for D-Cys has not been reported in the literature. It is well known that D-Cys is a powerful inhibitor of E. coli, some strains of which can have very serious effects on human

• ). Considering the fact that Cys is a trifunctional amino acid, it is interesting to unravel its binding mode with the cadmium-centred fluorescent chemosensor ACAQ. To shed light on the binding mechanism of Cys with the probe, seven other sulfur-containing molecules were chosen as control compounds (Table 3

Fluorometric recognition of both dihydrogen phosphate and iodide by a new flexible anthracene linked benzimidazolium-based receptor

• Kumaresh Ghosh and
• Debasis Kar

Beilstein J. Org. Chem. 2011, 7, 254–264, doi:10.3762/bjoc.7.34

• benzimidazolium group in the presence of a flexible spacer, we report herein the design and synthesis of a new chemosensor 1 (Figure 1), which shows selective recognition of dihydrogen phosphate in CH3CN among the other anions studied. The selectivity is changed on changing the polarity of the solvent, and the

A new fluorescent chemosensor for fluoride anion based on a pyrrole–isoxazole derivative

• Zhipei Yang,
• Kai Zhang,
• Fangbin Gong,
• Shayu Li,
• Jun Chen,
• Jin Shi Ma,
• Lyubov N. Sobenina,
• Albina I. Mikhaleva,
• Guoqiang Yang and
• Boris A. Trofimov

Beilstein J. Org. Chem. 2011, 7, 46–52, doi:10.3762/bjoc.7.8

• is brought about by deprotonation of the pyrrole-NH in receptor 1. Keywords: deprotonation; fluorescent chemosensor; fluoride anion recognition; Introduction The development of anion receptors has become a field of substantial interest and activity [1][2][3]. Among the various artificial receptors

• . This conclusion is also in agreement with the results of the 1H NMR titration experiment. Conclusion In conclusion, we report a new fluorescent chemosensor, pyrrole–isoxazole derivative, for fluoride recognition in CH3CN. The UV–vis and fluorescence titration experiments revealed that the receptor-NH

Molecular recognition of organic ammonium ions in solution using synthetic receptors

• Andreas Späth and
• Burkhard König

Beilstein J. Org. Chem. 2010, 6, No. 32, doi:10.3762/bjoc.6.32

• are deprotonated, which leads to lactone ring opening and the formation of a colored quinone conjugated carboxylate structure. The chemosensor discriminated terminal diamines by length: 1,8-diaminooctane (Kass = 1270 M−1) and 1,9-diaminononane (Kass = 2020 M−1) showed the highest binding constants in

• electron transfer (PET) is inhibited and the system shows an enhanced fluorescence. The binding was dependent on the chain length between the two cations, displaying a maximum stability in the case of the protonated 1,3-diaminopropane. for the bis(aza-15-crown-5) chemosensor 48a the following binding

Synthesis of indolo[3,2-b]carbazole-based new colorimetric receptor for anions: A unique color change for fluoride ions

• Ajit Kumar Mahapatra,
• Giridhari Hazra and
• Prithidipa Sahoo

Beilstein J. Org. Chem. 2010, 6, No. 12, doi:10.3762/bjoc.6.12

• Ajit Kumar Mahapatra Giridhari Hazra Prithidipa Sahoo Department of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711103, India, Tel.: +91 33 2668 4561; Fax: +91 33 2668 4564 10.3762/bjoc.6.12 Abstract A novel indolocarbazole-based chemosensor 1 containing hydrogen bond

• of over-accumulation [11]. This diversity of function, both beneficial and otherwise, makes the problem of fluoride ion detection of considerable interest. In this context, a colorimetric chemosensor is of particular interest due to its simplicity. Color changes that can be detected by the naked eye

• molecular receptor 1 for the selective sensing of anions by investigating the effect of the addition of tetrabutylammonium salts ([Bu4N]+X−, X = F−, Cl−, Br−, I−, AcO−, HSO4−, and H2PO4−). Receptor 1 (Figure 1) was particularly important as a chemosensor for fluoride owing to its noticeable color change in