Oxidation of [3]naphthylenes to cations and dications converts local paratropicity into global diatropicity

• Abel Cárdenas,
• Zexin Jin,
• Yong Ni,
• Jishan Wu,
• Yan Xia,
• Francisco Javier Ramírez and
• Juan Casado

Beilstein J. Org. Chem. 2025, 21, 277–285, doi:10.3762/bjoc.21.20

• antiaromatic precursors remain challenging to study. Haley and some of us reported the oxidization of partially antiaromatic diindenoanthracene, DIAn, Figure 1, forming charged molecules stabilized by the rearomatization of the central anthracene unit [13][14]. Porphyrinoid-based molecules [15][16][17] have

Advances in the use of metal-free tetrapyrrolic macrocycles as catalysts

• Mandeep K. Chahal

Beilstein J. Org. Chem. 2024, 20, 3085–3112, doi:10.3762/bjoc.20.257

• macrocycles as photocatalysts in organic synthesis, involving both single electron transfer (SET) and energy transfer (ET) mechanistic approaches [84]. This review does not only focus on the metal-free porphyrin macrocycles, but it also covers the area of different porphyrinoid systems, such as heteroatom

C–C Coupling in sterically demanding porphyrin environments

• Liam Cribbin,
• Brendan Twamley,
• Nicolae Buga,
• John E. O’ Brien,
• Raphael Bühler,
• Roland A. Fischer and
• Mathias O. Senge

Beilstein J. Org. Chem. 2024, 20, 2784–2798, doi:10.3762/bjoc.20.234

• coupling reactions, Suzuki–Miyaura couplings are known to be a robust tool when functionalizing porphyrins [29][30]. Many complex porphyrinoid architectures have been synthesized in this manner, from functional porphyrin arrays [31][32][33] to sterically challenging meso-substituted aryl bis-pocket

Radical reactivity of antiaromatic Ni(II) norcorroles with azo radical initiators

• Siham Asyiqin Shafie,
• Ryo Nozawa,
• Hideaki Takano and
• Hiroshi Shinokubo

Beilstein J. Org. Chem. 2024, 20, 1967–1972, doi:10.3762/bjoc.20.172

• Advanced Research, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi 464-8601, Japan 10.3762/bjoc.20.172 Abstract Norcorrole is a stable 16π-antiaromatic porphyrinoid that exhibits characteristic reactivities and physical properties. Here, we disclose the reaction of Ni(II) norcorroles with alkyl

• ) norcorrole. The radical reactivity of Ni(II) norcorroles was investigated by density functional theory (DFT) calculations. Keywords: 16π; antiaromatic; norcorrole; porphyrinoid; radical; Introduction Considerable attention has been directed toward antiaromatic norcorroles [1][2][3] due to the fascinating

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

• group worked on the alternative approach toward flexible iminoporphyrinoids built from tripyrrane [55][56]. They designed and synthesised the first porphyrinoid connecting the porphyrin and crown ether motifs within the macrocyclic framework [56]. This work laid a foundation for constructing crown

• ]. Sessler and co-workers reported on the synthesis of an expanded capped porphyrinoid [120]. The macrocycle incorporated the sapphyrin framework and was demonstrated to act as a ditopic receptor for ammonium fluoride binding cations in the crown ether pocket and fluoride interacting within the expanded

• presented a crown ether-expanded Schiff porphyrinoid synthesis [56]. Compound 15 incorporated a tripyrrane unit merged with an oligo(ethylene glycol) chain through imine linkages (Scheme 5). The hybrid comprised a core shared amongst a tripyrrane building block and a segment of crown ether linked through

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

• Rodrigo Costa e Silva,
• Luely Oliveira da Silva,
• Aloisio de Andrade Bartolomeu,
• Timothy John Brocksom and
• Kleber Thiago de Oliveira

Beilstein J. Org. Chem. 2020, 16, 917–955, doi:10.3762/bjoc.16.83

• continuous-flow photochemistry a sustainable alternative approach being applied already by the chemical and pharmaceutical industries. Porphyrinoid is the term given for a class of organic compounds containing four pyrrole rings connected by four methylene bridges, and include porphyrin, chlorin

• to regular N4-porphyrins (with four pyrrole units), but also can occur with other porphyrinoid compounds. Porphyrins containing other heteroatoms present physicochemical and electronic properties that are quite different from regular N4-porphyrins. These structures absorb and emit light at lower

Novel β-cyclodextrin–eosin conjugates

• Gábor Benkovics,
• Damien Afonso,
• András Darcsi,
• Szabolcs Béni,
• Sabrina Conoci,
• Éva Fenyvesi,
• Lajos Szente,
• Milo Malanga and
• Salvatore Sortino

Beilstein J. Org. Chem. 2017, 13, 543–551, doi:10.3762/bjoc.13.52

• effects (PDT and chemotherapy) have been developed by Král et al. [10][11]. The results achieved by these groups clearly demonstrated the numerous advantages of the PS–CD coupling. However, despite the number of porphyrinoid PSs conjugated with CDs [12][13][14][15][16][17][18][19][20], literature on

Easy access to heterobimetallic complexes for medical imaging applications via microwave-enhanced cycloaddition

• Nicolas Desbois,
• Sandrine Pacquelet,
• Adrien Dubois,
• Clément Michelin and
• Claude P. Gros

Beilstein J. Org. Chem. 2015, 11, 2202–2208, doi:10.3762/bjoc.11.239

• chosen two porphyrinoid derivatives that are easy to prepare in only a few steps: an azidocorrole 1 [9] and an azidoporphyrin 2 [10] (Figure 1). Porphyrins and corroles display interesting properties in terms of metal complexation of, e.g., transition metals. We have selected two commercial available

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