N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

• Fatemeh Doraghi,
• Seyedeh Pegah Aledavoud,
• Mehdi Ghanbarlou,
• Bagher Larijani and
• Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

• pyrrolines 62 were obtained by changing the reaction solvent to MeCN. Also, organic fluorophore compounds such as benzothienopyrrole and bis-thiolated boron dipyrromethene can be achieved from 3-thiolated pyrroles. Mechanistic studies showed that the oxidative species HNO and HCHO were generated through a

The B & B approach: Ball-milling conjugation of dextran with phenylboronic acid (PBA)-functionalized BODIPY

• Patrizia Andreozzi,
• Lorenza Tamberi,
• Elisamaria Tasca,
• Gina Elena Giacomazzo,
• Marta Martinez,
• Mirko Severi,
• Marco Marradi,
• Stefano Cicchi,
• Sergio Moya,
• Giacomo Biagiotti and
• Barbara Richichi

Beilstein J. Org. Chem. 2020, 16, 2272–2281, doi:10.3762/bjoc.16.188

• phenylboronic acid (PBA)-functionalized boron dipyrromethene (BODIPY) applying the ball milling approach. The ball milling formation of boron esters between PBA BODIPY and dextran proved to be more efficient in terms of reaction time, amount of reactants, and labelling degree compared to the corresponding

• with small molecules, in a green and scalable process. Results and Discussion The boron dipyrromethene dye 1 bearing a phenylboronic acid moiety (PBA) at the meso position of the BODIPY core (Scheme 1) was prepared in four synthetic steps starting from 4-formylbenzeneboronic acid (2) and pyrrole (3

Regioselectively α- and β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C–H functionalization and their photophysical properties

• Takahide Shimada,
• Shigeki Mori,
• Masatoshi Ishida and
• Hiroyuki Furuta

Beilstein J. Org. Chem. 2020, 16, 587–595, doi:10.3762/bjoc.16.53

• -materials. Keywords: alkynylation; BODIPY; direct C–H functionalization; gold(I); Introduction Boron-dipyrromethene (BODIPY, 1) and its derivatives are representative families of fluorophores that have been widely used in applications for bioimaging [1][2][3][4][5][6], photodynamic therapy [7][8][9][10

Functional panchromatic BODIPY dyes with near-infrared absorption: design, synthesis, characterization and use in dye-sensitized solar cells

• Quentin Huaulmé,
• Cyril Aumaitre,
• Outi Vilhelmiina Kontkanen,
• David Beljonne,
• Alexandra Sutter,
• Gilles Ulrich,
• Renaud Demadrille and
• Nicolas Leclerc

Beilstein J. Org. Chem. 2019, 15, 1758–1768, doi:10.3762/bjoc.15.169

• Polymères Université de Mons - UMONS / Materia Nova Place du Parc, 20, B-7000 Mons, Belgium ICPEES – UMR7515, CNRS-Université de Strasbourg, 25 rue Becquerel, 67087 Strasbourg CEDEX 02, France 10.3762/bjoc.15.169 Abstract We report two novel functional dyes based on a boron-dipyrromethene (BODIPY) core

• phthalocyanines [10][11], organic push–pull compounds [12], and boron-dipyrromethene [13] (BODIPY®). BODIPY dyes are one of the most extensively studied class of fluorophores due to their unique properties, including high absorption coefficients in the visible and NIR ranges, high fluorescence quantum yields, and

• were computed by density functional theory modelling (DFT) and characterized through UV–vis spectroscopy and cyclic voltammetry (CV) measurements. Finally, we report preliminary results obtained using these functional dyes as photosensitizers in dye-sensitized solar cells (DSSCs). Keywords: boron

Rational design of boron-dipyrromethene (BODIPY) reporter dyes for cucurbit[7]uril

• Mohammad A. Alnajjar,
• Jürgen Bartelmeß,
• Robert Hein,
• Pichandi Ashokkumar,
• Mohamed Nilam,
• Werner M. Nau,
• Knut Rurack and
• Andreas Hennig

Beilstein J. Org. Chem. 2018, 14, 1961–1971, doi:10.3762/bjoc.14.171

• Materialforschung und -prüfung (BAM), Richard-Willstätter-Str. 11, 12489 Berlin, Germany Laboratory of Bioimaging and Pathology, UMR 7021 CNRS, Faculty of Pharmacy, University of Strasbourg, 74 Route du Rhin, F-67401 Illkirch-Graffenstaden, France 10.3762/bjoc.14.171 Abstract We introduce herein boron

• -dipyrromethene (BODIPY) dyes as a new class of fluorophores for the design of reporter dyes for supramolecular host–guest complex formation with cucurbit[7]uril (CB7). The BODIPYs contain a protonatable aniline nitrogen in the meso-position of the BODIPY chromophore, which was functionalized with known binding

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

• against competing microorganisms was not the evolutionary driver for the emergence of the toxin. It is generally assumed in the literature that mycolactones reach their cellular targets by passive diffusion [91]. Based on competition experiments with the fluorescent, boron-dipyrromethene (BODIPY)-labeled

Benzothiadiazole oligoene fatty acids: fluorescent dyes with large Stokes shifts

• Lukas J. Patalag and
• Daniel B. Werz

Beilstein J. Org. Chem. 2016, 12, 2739–2747, doi:10.3762/bjoc.12.270

• as the carbohydrate part of glycolipids [7][8]. A further alternative is to render the lipid and especially the fatty acid part fluorescently active by the introduction of fluorescent moieties (Figure 1). Prominent examples in this area are NBD- (nitrobenzoxadiazole) [9][10], BODIPY- (boron

• -dipyrromethene) [11][12], BOIMPY- (bis(borondifluoride)-8-imidazodipyrromethene) [13] and pyrene-labeled fatty acids [14]. Of course, all these alterations might also affect the membrane structure and its dynamics. While the NBD-fluorophore suffers from unsuitable polarity, a pyrene motif disrupts the unpolar

Polythiophene and oligothiophene systems modified by TTF electroactive units for organic electronics

• Alexander L. Kanibolotsky,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1749–1766, doi:10.3762/bjoc.11.191

• units into a conjugated network is a standard way to narrow the HOMO/LUMO band gap and examples of such units include dioxopyrrolopyrrole (DPP) [17][18][19], benzodifuranone [20] and boron-dipyrromethene (BODIPY) [21][22]. As a different class of electroactive materials, TTF derivatives are well-known

Design, synthesis and photochemical properties of the first examples of iminosugar clusters based on fluorescent cores

• Mathieu L. Lepage,
• Antoine Mirloup,
• Manon Ripoll,
• Fabien Stauffert,
• Anne Bodlenner,
• Raymond Ziessel and
• Philippe Compain

Beilstein J. Org. Chem. 2015, 11, 659–667, doi:10.3762/bjoc.11.74

• insights into the multivalent effect observed in CFTR correcting activity. The originality of our approach relies on the fact that, in the structures designed, this is the scaffold itself [29][30], based on a pyrene or a boron-dipyrromethene (F-BODIPY) dye, which has fluorescence activity. Results and

• . Difluoroboradiaza-s-indacenes, commonly named boron-dipyrromethene dyes (F-BODIPY), were logically selected for the construction of the probes. These compounds indeed combine high fluorescence quantum yields and high molar extinction coefficients, strong chemical and photochemical stability in solution and in solid

Synthesis and properties of novel star-shaped oligofluorene conjugated systems with BODIPY cores

• Clara Orofino-Pena,
• Diego Cortizo-Lacalle,
• Joseph Cameron,
• Muhammad T. Sajjad,
• Pavlos P. Manousiadis,
• Neil J. Findlay,
• Alexander L. Kanibolotsky,
• Dimali Amarasinghe,
• Peter J. Skabara,
• Tell Tuttle,
• Graham A. Turnbull and
• Ifor D. W. Samuel

Beilstein J. Org. Chem. 2014, 10, 2704–2714, doi:10.3762/bjoc.10.285

• these two families were studied in order to determine their suitability as emissive materials in photonic applications. Keywords: absorption spectroscopy; BODIPY; cyclic voltammetry; photoluminescence; star-shaped oligofluorene; Introduction The boron-dipyrromethene (BODIPY) or 4,4-difluoro-4-bora-3a