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

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

• exhibit photophysical properties such as photosensitization [13], fluorescence, and aggregation-induced emission (AIE) [14][15][16]. π-Conjugated polycyclic hydrocarbons (CPHs) containing polycyclic heteroaromatic molecules (PHAs) and aza-polycyclic aromatic hydrocarbons (aza-PAHs) have been attracting

Photosensitized direct C–H fluorination and trifluoromethylation in organic synthesis

• Shahboz Yakubov and
• Joshua P. Barham

Beilstein J. Org. Chem. 2020, 16, 2151–2192, doi:10.3762/bjoc.16.183

• reactions. Keywords: C–H activation; energy transfer; fluorination; photocatalysis; photosensitization; visible light; Review 1 Introduction 1.1 Importance of direct C–H fluorination/trifluoromethylation and photosensitization in organic synthesis 1.1.1 Importance of fluorine atoms in organic molecules

• –H bond is matched to the HAT catalyst. For example, an electrophilic radical abstracts H atoms selectively from the most electron-rich or “hydridic” C–H bond [65]. 1.1.3 Importance of visible light and visible-light photosensitization in synthesis: Unlike many other traditional energy resources

• which the excited state photocatalyst participates directly in HAT with the substrate (Scheme 2B), herein termed PHAT [88]. iii) Photochemical reactions where the photosensitization catalyst (PSCat) engages in Dexter energy transfer (typically TTET) with the substrate (or fluorinating reagent) to induce

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

• Stephanie G. E. Amos,
• Marion Garreau,
• Luca Buzzetti and
• Jerome Waser

Beilstein J. Org. Chem. 2020, 16, 1163–1187, doi:10.3762/bjoc.16.103

Recent advances in photocatalyzed reactions using well-defined copper(I) complexes

• Mingbing Zhong,
• Xavier Pannecoucke,
• Philippe Jubault and
• Thomas Poisson

Beilstein J. Org. Chem. 2020, 16, 451–481, doi:10.3762/bjoc.16.42

• lactone synthesis using a copper-photocatalyzed PCET reaction. Photocatalytic Pinacol coupling reaction catalyzed by [Cu(I)(pypzs)(BINAP)]BF4. The ligands of the copper complex are omitted for clarity. Azide photosensitization using a Cu-based photocatalyst. Funding This work was partially supported by

p-Pyridinyl oxime carbamates: synthesis, DNA binding, DNA photocleaving activity and theoretical photodegradation studies

• Panagiotis S. Gritzapis,
• Panayiotis C. Varras,
• Nikolaos-Panagiotis Andreou,
• Katerina R. Katsani,
• Konstantinos Dafnopoulos,
• George Psomas,
• Zisis V. Peitsinis,
• Alexandros E. Koumbis and
• Konstantina C. Fylaktakidou

Beilstein J. Org. Chem. 2020, 16, 337–350, doi:10.3762/bjoc.16.33

• nucleases [13][14]. The interaction of molecules with DNA and their affinity towards this macromolecule also plays a key role in photosensitization techniques. Light activated oxidative DNA cleaving agents are called “DNA photocleavers”. These compounds are able to absorb light and to be selectively excited

Dyes in modern organic chemistry

• Heiko Ihmels

Beilstein J. Org. Chem. 2019, 15, 2798–2800, doi:10.3762/bjoc.15.272

• are found in nature, thus establishing important classes of dyes based on natural products [15][16]. At the same time, dyes themselves turned out to be useful tools in organic synthesis, for example, in traditional photosensitization or in a more recent topical approach as efficient and highly

Excited state dynamics for visible-light sensitization of a photochromic benzil-subsituted phenoxyl-imidazolyl radical complex

• Yoichi Kobayashi,
• Yukie Mamiya,
• Katsuya Mutoh,
• Hikaru Sotome,
• Masafumi Koga,
• Hiroshi Miyasaka and
• Jiro Abe

Beilstein J. Org. Chem. 2019, 15, 2369–2379, doi:10.3762/bjoc.15.229

• energy level of PIC is estimated to be 63 kcal mol−1. It suggests that the T1 state energy level of benzil is slightly lower than that of PIC. Moreover, the triplet photosensitization was examined by the microsecond transient absorption measurements of the mixture solution of benzil and PIC in benzene

• , most of the photochromic reaction is induced via the Dexter-type singlet–singlet energy transfer from the benzil to the PIC units with the time constant of 38 ps. The triplet photosensitization does not occur in Benzil-PIC most probably because the triplet energy level of the PIC unit is higher than

Photochemical generation of the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radical from caged nitroxides by near-infrared two-photon irradiation and its cytocidal effect on lung cancer cells

• Ayato Yamada,
• Manabu Abe,
• Yoshinobu Nishimura,
• Shoji Ishizaka,
• Masashi Namba,
• Taku Nakashima,
• Kiyofumi Shimoji and
• Noboru Hattori

Beilstein J. Org. Chem. 2019, 15, 863–873, doi:10.3762/bjoc.15.84

• 2a induced cancer cell death in vitro, although no in vivo study was performed because of the low water solubility of 2a. At this point, we cannot rule out generate of ROS by photosensitization of the chromophore in the presence of O2 for the cytotoxicity. Conclusion In the present study, novel caged

Learning from B₁₂ enzymes: biomimetic and bioinspired catalysts for eco-friendly organic synthesis

• Keishiro Tahara,
• Ling Pan,
• Toshikazu Ono and
• Yoshio Hisaeda

Beilstein J. Org. Chem. 2018, 14, 2553–2567, doi:10.3762/bjoc.14.232

• iridium(III) complexes such as Irdfppy [112] are superior to [Ru(bpy)3]Cl2 in terms of their photosensitization abilities in visible-light-driven B12 catalytic systems (Scheme 9) [104]. This was probably due to the gradual decomposition of [Ru(bpy)3]Cl2 under visible light irradiation. This is consistent

Synthesis and photophysical studies of a multivalent photoreactive Ru^II-calix[4]arene complex bearing RGD-containing cyclopentapeptides

• Sofia Kajouj,
• Lionel Marcelis,
• Alice Mattiuzzi,
• Adrien Grassin,
• Damien Dufour,
• Pierre Van Antwerpen,
• Didier Boturyn,
• Eric Defrancq,
• Mathieu Surin,
• Julien De Winter,
• Pascal Gerbaux,
• Ivan Jabin and
• Cécile Moucheron

Beilstein J. Org. Chem. 2018, 14, 1758–1768, doi:10.3762/bjoc.14.150

• upon light irradiation. Two types of photooxidative damages can be induced: (i) by photosensitization of singlet oxygen and subsequent generation of highly reactive oxygen species (ROS) (type I photosensitization) or (ii) by direct oxidative electron transfer to biological molecules such as DNA or

• amino acids (type II photosensitization). In particular, it was shown that RuII complexes containing at least two highly π-deficient polyazaaromatic ligands such as 1,4,5,8-tetraazaphenanthrene (TAP) [12][13][14] or 1,4,5,8,9,12-hexaazatriphenylene (HAT) [15] are able to oxidize the guanine base (G) of

Interactions of cyclodextrins and their derivatives with toxic organophosphorus compounds

• Sophie Letort,
• Sébastien Balieu,
• William Erb,
• Géraldine Gouhier and
• François Estour

Beilstein J. Org. Chem. 2016, 12, 204–228, doi:10.3762/bjoc.12.23

• included pesticides, following the order α < γ < β. It seems that this promotive effect relies on the CDs’ ability to complex both the organophosphorus pesticides and the reactive radical resulting from the photosensitization of humic acids. As the promotion effect of CDs follows the order α < γ < β, it

An integrated photocatalytic/enzymatic system for the reduction of CO₂ to methanol in bioglycerol–water

• Michele Aresta,
• Angela Dibenedetto,
• Tomasz Baran,
• Antonella Angelini,
• Przemysław Łabuz and
• Wojciech Macyk

Beilstein J. Org. Chem. 2014, 10, 2556–2565, doi:10.3762/bjoc.10.267

• . Keywords: CO2 chemistry; electron transfer; enzymatic CO2 reduction; NADH regeneration; photochemistry; photosensitization; Introduction The reduction of CO2 to fuel is a technology that could contribute to the recycling of large quantities of carbon. Among the various routes, the enzymatic reduction of

Cyclodextrin nanosponge-sensitized enantiodifferentiating photoisomerization of cyclooctene and 1,3-cyclooctadiene

• Wenting Liang,
• Cheng Yang,
• Masaki Nishijima,
• Gaku Fukuhara,
• Tadashi Mori,
• Andrea Mele,
• Franca Castiglione,
• Fabrizio Caldera,
• Francesco Trotta and
• Yoshihisa Inoue

Beilstein J. Org. Chem. 2012, 8, 1305–1311, doi:10.3762/bjoc.8.149

• ] (Scheme 1). Enantiodifferentiating photosensitization of 1Z and 2ZZ was extensively studied by using different kinds of conventional and supramolecular chiral photosensitizers (Scheme 2). The enantioselectivity obtained is generally low to moderate, despite that fact that some reactions were performed at

• convenient and also powerful tool for manipulating the stereochemical outcomes of supramolecular photochirogenesis. It should be noted that γ-CD-based nanosponge 5 gave the highest ee values for both 1E and 2EZ. This is in sharp contrast to the result reported for the photosensitization with conventional

• sensitizer-modified CDs [9][39], in which the more size-matched β-CD, rather than the larger-sized γ-CD, sensitizers consistently afforded 1E and 2EZ in (much) higher ee’s. This unusual behavior observed for β- and γ-CDNSs implies the operation of photosensitization and/or enantiodifferentiation mechanisms

Triple-channel microreactor for biphasic gas–liquid reactions: Photosensitized oxygenations

• Ram Awatar Maurya,
• Chan Pil Park and
• Dong-Pyo Kim

Beilstein J. Org. Chem. 2011, 7, 1158–1163, doi:10.3762/bjoc.7.134

• oxygenations of α-terpinene, citronellol, and allyl alcohols. Keywords: gas–liquid reaction; microreactor; photosensitization; singlet oxygen; Introduction Microreactors have recently attracted much interest among the scientific community for performing laboratory operations on small scales [1][2][3][4][5][6

Supramolecular FRET photocyclodimerization of anthracenecarboxylate with naphthalene-capped γ-cyclodextrin

• Qian Wang,
• Cheng Yang,
• Gaku Fukuhara,
• Tadashi Mori,
• Yu Liu and
• Yoshihisa Inoue

Beilstein J. Org. Chem. 2011, 7, 290–297, doi:10.3762/bjoc.7.38

• far examined in aqueous solutions [20][22]. We further examined indirect FRET excitation (intramolecular photosensitization) of AC included in host 6. Mechanistically, FRET excitation of AC is highly advantageous from the photochirogenic point of view, since the static energy transfer to an AC

Synthesis of cationic dibenzosemibullvalene-based phase-transfer catalysts by di-π-methane rearrangements of pyrrolinium-annelated dibenzobarrelene derivatives

• Heiko Ihmels and
• Jia Luo

Beilstein J. Org. Chem. 2011, 7, 119–126, doi:10.3762/bjoc.7.17

• solvent, the two semibullvalenes 3gI and 3gII were formed in a 45:55 ratio; however, attempts to separate the two regioisomers by chromatography were unsuccessful (Scheme 4). Derivative 2g was also photoinert in the solid-state. The lack of internal photosensitization of derivative 2g resembles the