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

• toluene. This phenomenon aligns with the notion that the TICT states experience stabilization with increasing solvent polarity. Conversely, in contrast to 68–70, and 71, a TCBD derivative 72 incorporating a tetraphenylethylene (TPE) moiety exhibited no emission in toluene, possibly due to the presence of

pH-Responsive fluorescent supramolecular nanoparticles based on tetraphenylethylene-labelled chitosan and a six-fold carboxylated tribenzotriquinacene

• Nan Yang,
• Yi-Yan Zhu,
• Wei-Xiu Lin,
• Yi-Long Lu and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2023, 19, 635–645, doi:10.3762/bjoc.19.45

• , PR China 10.3762/bjoc.19.45 Abstract We synthesized a new tetraphenylethylene-modified chitosan bioconjugate, CS-TPE, that shows the aggregation-induced emission effect. It can self-assemble into fluorescent polymeric nanoparticles in an aqueous solution at pH 5.3 either alone or with the water

• fluorescence emission based on CS-TPE or TBTQ-C6/CS-TPE may find applications in various fields, including the development of visual oral drug delivery systems. Keywords: chitosan; nanoparticle; tetraphenylethylene; tribenzotriquinacene; Introduction Stimuli-responsive assemblies in aqueous media have drawn

• , conventional fluorescent dyes exhibit aggregation-caused quenching (ACQ) when introduced into nanoparticles at high loads, resulting in poor fluorescence imaging quality. In recent years, tetraphenylethylene (TPE)-based dyes have been frequently used to overcome the ACQ problem due to their unique aggregation

Supramolecular approaches to mediate chemical reactivity

• Pablo Ballester,
• Qi-Qiang Wang and
• Carmine Gaeta

Beilstein J. Org. Chem. 2022, 18, 1463–1465, doi:10.3762/bjoc.18.152

• -workers [19] reported an efficient photocatalytic supramolecular system based on a self-assembled nanosystem. The self-assembled system was obtained in an aqueous medium by inclusion of ammonium benzoyl-ʟ-alaninate (G) in a tetraphenylethylene-embedded pillar[5]arene (m-TPEWP5). The resulting worm-like

Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistry

• Koji Kubota,
• Emiru Baba,
• Tamae Seo,
• Tatsuo Ishiyama and
• Hajime Ito

Beilstein J. Org. Chem. 2022, 18, 855–862, doi:10.3762/bjoc.18.86

• ), tetraphenylethylene (1l), and anthracene (1m) reacted with diboron 2 to form the desired products (3f–m) in high yields. Next, the substrate scope of liquid aryl bromides was investigated (Scheme 3). We found that the present mechanochemical conditions were applicable to the solid substrate and various liquid

Tetraphenylethylene-embedded pillar[5]arene-based orthogonal self-assembly for efficient photocatalysis in water

• Zhihang Bai,
• Krishnasamy Velmurugan,
• Xueqi Tian,
• Minzan Zuo,
• Kaiya Wang and
• Xiao-Yu Hu

Beilstein J. Org. Chem. 2022, 18, 429–437, doi:10.3762/bjoc.18.45

• supramolecular self-assembled nanosystem based on host–guest interactions between water-soluble tetraphenylethylene-embedded pillar[5]arene (m-TPEWP5) and ammonium benzoyl-ʟ-alaninate (G) in an aqueous medium. The obtained assembly of m-TPEWP5 and G showed aggregation-induced emission (AIE) via the blocking of

• supramolecular assembly with a two-step FRET process by the utilization of a metallacycle-tetraphenylethylene (TPE) donor and eosin Y (EsY) and sulforhodamine (SR101) as first and second acceptors, respectively. The resulting supramolecular energy transfer system was applied to the alkylation of C–H bonds via a

Complexation of a guanidinium-modified calixarene with diverse dyes and investigation of the corresponding photophysical response

• Yu-Ying Wang,
• Yong Kong,
• Zhe Zheng,
• Wen-Chao Geng,
• Zi-Yi Zhao,
• Hongwei Sun and
• Dong-Sheng Guo

Beilstein J. Org. Chem. 2019, 15, 1394–1406, doi:10.3762/bjoc.15.139

• intramolecular charge-transfer dyes. Phosphated tetraphenylethylene was involved as the classical aggregation-induced emission dye. Sulfonated acedan representing one example of two-photon fluorescent probes, was also investigated. A ruthenium(II) complex with carboxylated bipyridyl ligands was included as a

• (EY), rose bengal (RB), tetraphenylporphine sulfonate (TPPS), sulfonated aluminum phthalocyanine (AlPcS4), 2-(p-toluidinyl)naphthalene-6-sulfonic acid (2,6-TNS), 1-anilinonaphthalene-8-sulfonic acid (1,8-ANS), phosphated tetraphenylethylene (P-TPE), sulfonated acedan (TPS), and a ruthenium(II) complex

• biosensors [49][53]. Tetraphenylethylene (TPE) and its derivatives represent a classical family of AIEgens due to their simple synthesis. In TPE, four phenyl rings are linked to the central olefin through single bonds. As isolated molecule, the phenyl rings have great freedom to rotate or twist against the

A novel application of 2-silylated 1,3-dithiolanes for the synthesis of aryl/hetaryl-substituted ethenes and dibenzofulvenes

• Grzegorz Mlostoń,
• Paulina Pipiak,
• Róża Hamera-Fałdyga and
• Heinz Heimgartner

Beilstein J. Org. Chem. 2017, 13, 1900–1906, doi:10.3762/bjoc.13.185

• the reagents in a ratio of 3:1. Under these conditions, 1,3-dithiolane 6a was formed almost exclusively with only traces of 1,4-dithiane 7 as revealed by 1H NMR analysis of the crude reaction mixture. Desilylation of 6a occurred quantitatively and the known tetraphenylethylene (9a) [26] was obtained

Photoreactions of cyclic sulfite esters: Evidence for diradical intermediates

• Rick C. White,
• Benny E. Arney Jr. and
• Heiko Ihmels

Beilstein J. Org. Chem. 2012, 8, 1208–1212, doi:10.3762/bjoc.8.134

• tetraphenylethylene, the latter has not been detected [16]. The formation of 10 may be explained by the additional phenyl substituent, as compared to the cyclic sulfite 8, which apparently facilitates the elimination of SO3 to give stilbene (10). Firstly, the phenyl substituent leads to a significant stabilization of