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

• zinc cations to align 1.1 through the formation of hydrogen-bonded coordination complexes. Thus, when a single crystal of the [Zn(bpe)2(H2O)4](NO3)2·8/3H2O·2/3bpe complex was exposed to UV irradiation (dark blue phosphor lamps, λ = 350 nm) for 25 h, only 46% conversion to 1.2 was observed via 1H NMR

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

• from certain plant species (Figure 1) [12]. The acenaphthylene-fused thiophene-based heteroarene 3 is another heterocyclic fluoranthene analogue, which was used as an organic semiconductor in transistors [13]. The synthesis and coordination complexes of the acenaphthylene-fused N-heterocyclic (NHC

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

• such as K+, NH4+, and Ba2+ required two crown ether cavities attached to the porphyrin to form the coordination complexes through the dimerisation of the macrocycle. The dimensions of the crown ether pocket determined the complex formation; for example, if there was a mismatch in the sizes of the

Synthesis of dibenzosuberenone-based novel polycyclic π-conjugated dihydropyridazines, pyridazines and pyrroles

• Ramazan Koçak and
• Arif Daştan

Beilstein J. Org. Chem. 2021, 17, 719–729, doi:10.3762/bjoc.17.61

• biochemical studies on these compounds, which have the potential to be used in chemosensors, light harvesting, organic optoelectronics, metal coordination complexes and other photophysical applications and in biological systems. Structures of dibenzosuberenone 1 and pyridazine and pyrrole derivatives

Recent developments in enantioselective photocatalysis

• Callum Prentice,
• James Morrisson,
• Andrew D. Smith and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2020, 16, 2363–2441, doi:10.3762/bjoc.16.197

• desired products 267 or 268 in moderate yields and enantioselectivities (3 examples, up to 75:25 er for 267 and 2 examples, up to 68:32 er for 268). Lewis acid catalysis Lewis acids have been known for decades to activate carbonyl compounds through the formation of coordination complexes that increases

A chiral self-sorting photoresponsive coordination cage based on overcrowded alkenes

• Constantin Stuckhardt,
• Diederik Roke,
• Wojciech Danowski,
• Edwin Otten,
• Sander J. Wezenberg and
• Ben L. Feringa

Beilstein J. Org. Chem. 2019, 15, 2767–2773, doi:10.3762/bjoc.15.268

• supramolecular coordination complexes consisting of a Pd2L4 stoichiometry. As shown by NMR, CD and X-ray studies, as well as DFT calculations, these complexes form cage-like structures by chiral self-sorting. Photochromic ligands derived from first generation molecular motors enable light-driven interconversion

• coordination complexes (SCCs) represent a promising class of compounds which have been used in a variety of molecular systems [1][2][3][4][5][6]. Taking advantage of the vacant cavity inside these complexes, SCCs have been applied in drug delivery [6][7][8], supramolecular catalysis [9][10][11][12], X-ray

• interesting strategy to form responsive coordination complexes, as they feature a large geometric change upon switching [47]. Herein, we report a photoresponsive coordination cage with ligands based on a first generation molecular motor (Figure 1). Cages with a Pd2L4 composition are formed from bidentate

Self-assembled coordination thioether silver(I) macrocyclic complexes for homogeneous catalysis

• Zhen Cao,
• Aline Lacoudre,
• Cybille Rossy and
• Brigitte Bibal

Beilstein J. Org. Chem. 2019, 15, 2465–2472, doi:10.3762/bjoc.15.239

• the stoichiometry of coordination complexes. Atropisomer 1 directed the self-assembly towards the same half-space (regarding the anthracene core). The triflate anion lead to a [2 + 2] macrocycle meanwhile the more coordinating nitrate anion induced the formation of a large globular macrocycle M6L4. A

2,3-Dibutoxynaphthalene-based tetralactam macrocycles for recognizing precious metal chloride complexes

• Li-Li Wang,
• Yi-Kuan Tu,
• Huan Yao and
• Wei Jiang

Beilstein J. Org. Chem. 2019, 15, 1460–1467, doi:10.3762/bjoc.15.146

• sidewalls have been synthesized and characterized. The macrocycle containing isophthalamide bridges can bind square-planar chloride coordination complexes of gold(III), platinum(II), and palladium(II) in CDCl3, while the macrocycle with 2,6-pyridine dicarboxamide bridging units cannot. This may be due to

• macrocycle, which make it conformationally adaptive to maximize the binding affinities. In addition, the macrocycle shows fluorescent quenching when adding the chloride metal complexes in its solution and may be used as a fluorescent sensor for the detection of these coordination complexes. Keywords: host

• a pair of new tetralactam macrocycles with 2,3-dibutoxynaphthalene as the sidewalls. The tetralactam macrocycle with 2,6-pyridine dicarboxamide cannot bind square-planar chloride coordination complexes of gold(III), platinum(II), and palladium(II) in CDCl3, while the macrocycle containing

Design of a double-decker coordination cage revisited to make new cages and exemplify ligand isomerism

• Sagarika Samantray,
• Sreenivasulu Bandi and
• Dillip K. Chand

Beilstein J. Org. Chem. 2019, 15, 1129–1140, doi:10.3762/bjoc.15.109

• ]. Complexation of cis-protected palladium(II), i.e., (PdL’) or bare palladium(II) with non-chelating bidentate ligands is known to afford a series of (PdL’)mLm or PdmL2m-type self-assembled coordination complexes [5]. Pd2L4-type cages are the simplest representatives among the PdmL2m-type complexes, yet most

• , though in small proportions, using ligand L1 but not L2. The ligands L1 and L2 are positional isomers (regioisomers) hence many of their complexes could be rightfully considered under ligand isomerism in coordination complexes. Experimental Synthesis of ligand L1: A mixture of pyridine-3,5-diyldimethanol

• ’ (Supporting Information File 1, Figure S69) showed isotopic peak pattern at m/z = 991.51 which corresponds to the cationic fragment [7a’ − 2NO3]2+ that is formed due to the loss of two units of counter anions from 7a’. The experimental and theoretical peak patterns were found to be in agreement. Coordination

Selective benzylic C–H monooxygenation mediated by iodine oxides

• Kelsey B. LaMartina,
• Haley K. Kuck,
• Linda S. Oglesbee,
• Asma Al-Odaini and
• Nicholas C. Boaz

Beilstein J. Org. Chem. 2019, 15, 602–609, doi:10.3762/bjoc.15.55

• substrate containing benzylic C–H bonds with acidic sodium dichromate or basic potassium permanganate [3][4][5]. More recent examples have used metal coordination complexes as catalysts for oxidation [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20]. Additionally, transition metal-based complexes are

Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines

• Andrejs Šišuļins,
• Jonas Bucevičius,
• Yu-Ting Tseng,
• Irina Novosjolova,
• Kaspars Traskovskis,
• Ērika Bizdēna,
• Huan-Tsung Chang,
• Sigitas Tumkevičius and
• Māris Turks

Beilstein J. Org. Chem. 2019, 15, 474–489, doi:10.3762/bjoc.15.41

• as cell imaging tools [31][32], biosensors and sensors for detection of heavy metals [33]. The tendency of these structures to form hydrogen bonds, to respond to medium effects (solvatochromism) [34] and to certain impurities (e.g., coordination complexes with metal ions) make these compound classes

Bi-mediated allylation of aldehydes in [bmim][Br]: a mechanistic investigation

• Mrunesh Koli,
• Sucheta Chatterjee,
• Subrata Chattopadhyay and
• Dibakar Goswami

Beilstein J. Org. Chem. 2018, 14, 2198–2203, doi:10.3762/bjoc.14.193

• . Nonetheless, the 1H NMR spectral pattern clearly indicated formation of η1-Bi-allyl coordination complexes. To the best of our knowledge, simultaneous formation of two allylbismuth species in any media is unprecedented. To see the reactivity of the species I and II, benzaldehyde (1a) was added at −70 °C to

Exploring mechanochemistry to turn organic bio-relevant molecules into metal-organic frameworks: a short review

• Vânia André,
• Sílvia Quaresma,
• João Luís Ferreira da Silva and
• M. Teresa Duarte

Beilstein J. Org. Chem. 2017, 13, 2416–2427, doi:10.3762/bjoc.13.239

• we will just present a few examples herein. It is common that these compounds are reported as coordination networks, or metallopharmaceuticals. One example we would like to mention has been proposed by Braga et al. [111], in which gabapentin was used as linker to build two new coordination complexes

• compounds with gabapentin was based on studies concerning the understanding of the physiological and pathophysiological roles played by Zn2+ and Cu2+ in various biological systems [121][122][123], and therefore the use of such coordination complexes was envisaged a new route for the delivery of those drugs

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

• occasionally applied to coordination complexes bearing a phosphonate function as exemplified with compound 20 [123]. HBr was used more occasionally to hydrolyze phosphonates [124][125][126]. Regarding the nature of the alkyl chains of dialkyl phosphonates, it must be noted that most of the time these chains

Smart molecules for imaging, sensing and health (SMITH)

• Bradley D. Smith

Beilstein J. Org. Chem. 2015, 11, 2540–2548, doi:10.3762/bjoc.11.274

• on the cell surface during the process of apoptosis or programmed cell death. Thus, phosphatidylserine is an excellent biomarker of cell death and an attractive target for molecular imaging. We reasoned that synthetic anion receptors such as zinc dipicolylamine (ZnDPA) coordination complexes would

Mechanical stability of bivalent transition metal complexes analyzed by single-molecule force spectroscopy

• Manuel Gensler,
• Christian Eidamshaus,
• Maurice Taszarek,
• Hans-Ulrich Reissig and
• Jürgen P. Rabe

Beilstein J. Org. Chem. 2015, 11, 817–827, doi:10.3762/bjoc.11.91

• and understand the mechanical properties of multivalent systems through well-characterized model systems. We analyzed the rupture behavior of three different bivalent pyridine coordination complexes with Cu2+ in aqueous environment by single-molecule force spectroscopy. Those complexes share the same

• bifunctional PEG as written above. Figure 1 shows the expected coordination complexes of our mono- and bivalent model systems with Cu2+ in aqueous solution. In the present work, we analyzed the bivalent systems 2b and 2c by DFS, similarly as for the recently published reference case of 2a [27]. We modified

• partially due to the fact that the π–π-stacking of pyridines [50] was a competing interaction. The most probable rupture force, used in the KBE model, was due to the coordination complexes. Methods using the whole data set are strongly influenced by the stacking interaction and would have needed heavily

cis–trans Isomerization of silybins A and B

• Michaela Novotná,
• Radek Gažák,
• David Biedermann,
• Florent Di Meo,
• Petr Marhol,
• Marek Kuzma,
• Lucie Bednárová,
• Kateřina Fuksová,
• Patrick Trouillas and
• Vladimír Křen

Beilstein J. Org. Chem. 2014, 10, 1047–1063, doi:10.3762/bjoc.10.105

• isomerization can be initiated by the formation of coordination complexes at either C-4=O or O-1 (see Scheme 5). Nevertheless, based on the quantum chemical calculations (Table 3 and Table 4) together with the representation of cis-isomers in the isomerization mixture, the most stable coordination complex IIa

Silica: An efficient catalyst for one-pot regioselective synthesis of dithioethers

• Samir Kundu,
• Babli Roy and
• Basudeb Basu

Beilstein J. Org. Chem. 2014, 10, 26–33, doi:10.3762/bjoc.10.5

• food-processing industry [4][5][6][7][8]. For example, organosulfur compounds in garlic are often used in food-processing industries as flavouring and preservative agents and are also used as herbal medicine [4]. Dithioethers are commonly employed as ligands in preparing metal-coordination complexes

Spin state switching in iron coordination compounds

• Philipp Gütlich,
• Ana B. Gaspar and
• Yann Garcia

Beilstein J. Org. Chem. 2013, 9, 342–391, doi:10.3762/bjoc.9.39

• consequences of ST are depicted in Figure 1 [23]. Thermal spin transition occurs nearly exclusively with coordination complexes of 3d metal ions. This is not expected for 4d and 5d transition element compounds on the basis of ligand field theory, because the strength of the ligand field increases notably (by

Functional properties of metallomesogens modulated by molecular and supramolecular exotic arrangements

• Alessandra Crispini,
• Mauro Ghedini and
• Daniela Pucci

Beilstein J. Org. Chem. 2009, 5, No. 54, doi:10.3762/bjoc.5.54

• different functionalities and inducing non-conventional shapes and properties in the resulting complexes. Our strategy was based on the synthesis of mesogenic coordination complexes whose molecular architectures are controlled by the modulation of different and tunable molecular motifs: the nature of the

• single molecule to supramolecular network, confirming that metal coordination provides a helpful tool for obtaining multifunctional soft materials. Keywords: coordination complexes; functionality; liquid crystals; metallomesogens; Introduction Recent interest in designing novel soft and functional