Perspectives on push–pull chromophores derived from click-type [2 + 2] cycloaddition–retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes

• Michio Yamada

Beilstein J. Org. Chem. 2024, 20, 125–154, doi:10.3762/bjoc.20.13

• ]. In addition to anilino groups, a myriad of donor entities, including urea-substituted phenyl groups [18][19], carbazoles [20], phenothiazines [21][22], thiophenes [23][24][25][26], tetrathiafulvalenes (TTFs) [27], extended TTFs [28], ferrocenes [27][29][30][31][32][33][34][35][36][37][38][39][40][41

N-Arylphenothiazines as strong donors for photoredox catalysis – pushing the frontiers of nucleophilic addition of alcohols to alkenes

• Fabienne Speck,
• David Rombach and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2019, 15, 52–59, doi:10.3762/bjoc.15.5

• optoelectronic properties of the molecules. Photochemical methods have allowed to overcome some of the current limitations in thermally driven chemistry and to substitute conventional energy demanding chemistry by highly sustainable photochemical methods [3][4][5][6][7][8][9][10][11][12]. Phenothiazines have

• with a small S0–S1 gap for the development of strongly reducing photoredox catalysts. Thus, we first focused our strategy in catalyst development on the synthesis of some highly electron-rich phenothiazines 2–5 as well as some electron-deficient phenothiazines 6–9 to analyze the influences of

• phenothiazines 2, 10 and 11 showed no significant change in the absorption maximum of the S1 transition (10 in comparison to 2), but replacement of the methyl groups by branched isobutyl groups in 11 resulted in a hypsochromic shift of the bathochromic features of absorption. The nitro compound 6 turned out to

The design and synthesis of an antibacterial phenothiazine–siderophore conjugate

• Abed Tarapdar,
• James K. S. Norris,
• Oliver Sampson,
• Galina Mukamolova and
• James T. Hodgkinson

Beilstein J. Org. Chem. 2018, 14, 2646–2650, doi:10.3762/bjoc.14.242

• conjugates can demonstrate enhanced uptake and internalisation to the bacterial cell resulting in significantly reduced MIC values and extended spectrum of activity. Phenothiazines are a class of small molecules that have been identified as a potential treatment for multidrug resistant tuberculosis and

• ]. Phenothiazines are a privileged scaffold in drug discovery most noted for their use as antipsychotic drugs including chlorpromazine, trifluoperazine, and thioridazine. However, such drugs have also long been noted for their significant antimicrobial activity particularly against Staphylococcus aureus and

• Mycobacterium tuberculosis [9][10]. The emergence of MDR-TB has led to structure–activity studies to enhance the antitubercular activity of phenothiazines leading to the identification of chlorpromazine analogue 1 (Figure 1) which demonstrates MIC values comparable to first-line TB drugs in vitro [11]. However

Fluorescent nucleobase analogues for base–base FRET in nucleic acids: synthesis, photophysics and applications

• Mattias Bood,
• Sangamesh Sarangamath,
• Moa S. Wranne,
• Morten Grøtli and
• L. Marcus Wilhelmsson

Beilstein J. Org. Chem. 2018, 14, 114–129, doi:10.3762/bjoc.14.7

• developing the family of fluorescent base analogues known as the tricyclic cytosines (tC) [14][29][30][31][35][36][37][38]. The aromatic core of tC was first prepared by Roth et al. in 1963 as part of a study to obtain pharmacologically active compounds structurally similar to phenothiazines [39]. Compound 1

Thiophene-forming one-pot synthesis of three thienyl-bridged oligophenothiazines and their electronic properties

• Dominik Urselmann,
• Konstantin Deilhof,
• Bernhard Mayer and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2016, 12, 2055–2064, doi:10.3762/bjoc.12.194

• ; copper; cyclic voltammetry; DFT; microwave-assisted synthesis; multicomponent reactions; palladium; phenothiazines; thiophenes; Introduction Oligothiophenes [1][2][3][4][5][6][7][8] have adopted a dominating role among functional π-electron systems [9]. In particular, they have received attention as

• [53][54][55] substituted (oligo)phenothiazines. Their pronounced reversible oxidation potentials, their electro- and photochromicity [56], and their luminescence [57][58] have rendered (oligo)phenothiazines interesting candidates as donors in donor–acceptor conjugates with photo-induced electron

• -transfer characteristics [59][60][61][62][63], as hole-transport materials [64], for applications in mesoporous organo silica hybrid materials [65], and as chromophores in dye-sensitized solar cells [66][67][68]. Furthermore, (oligo)phenothiazines in their native reduced forms display a pronounced ability

Rearrangements of organic peroxides and related processes

• Ivan A. Yaremenko,
• Vera A. Vil’,
• Dmitry V. Demchuk and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162

• peroxides (Scheme 61) [331]. The direct dehydrogenative construction of C–N bonds between unprotected phenols 215 and a series of 10H-phenoxazines and 10H-phenothiazines 214 with formation of 216 was carried out using a Hock-like activation with O2 followed by amine oxidation (Scheme 62) [332]. The Hock

Synthesis, electronic properties and self-assembly on Au{111} of thiolated (oligo)phenothiazines

• Adam W. Franz,
• Svetlana Stoycheva,
• Michael Himmelhaus and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2010, 6, No. 72, doi:10.3762/bjoc.6.72

• presence of a gold-coated silicon wafer. Monolayer formation is confirmed by ellipsometry and the results compared to those obtained by force field and DFT calculations. Keywords: cyclic voltammetry; ellipsometry; phenothiazines; SAM; thiols; Introduction Functional organic π-systems [1] are of great

• conductive molecular wires investigated. Among many heteroaromatic systems, phenothiazines, their derivatives and oligomers are interesting building blocks for rigid-rod and wire-like molecular modules for single-molecule electronics as a consequence of their electronic properties. In particular, their

• conformation of phenothiazines [36], with a folding angle of 158.5°, represents an intriguing new aspect for the formation of self-assembled monolayers (SAMs) of this class of compounds. Furthermore, the transformation of phenothiazines into stable planar radical cations with excellent delocalization [37