Synthesis, Properties, and Structures of Functionalized <i>peri</i>-Xanthenoxanthene

Lv, Na; Xie, Meilan; Gu, Weibing; Ruan, Huanyang; Qiu, Song; Zhou, Changlin; Cui, Zheng

doi:10.1021/ol400790d

Cited by 47 publications

(36 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The synthesis started from enantiomerically pure BINOL ( 1 ). Bromination and subsequent methoxymethyl ether (MOM) protection of the phenolic groups yielded 2 . The key step of the synthesis was the two‐step, one‐pot Suzuki–Miyaura cross‐coupling to form 3 via the doubly borylated BINOL intermediate in a satisfactory yield of 76 % for four synthetic transformations.…”

Section: Resultsmentioning

confidence: 99%

Diastereoselective Formation of Homochiral Helicates through Subcomponent Self‐Assembly

et al. 2017

View full text Add to dashboard Cite

Homochiral helicates were prepared through subcomponent self‐assembly with a C2‐symmetric chiral building block based on a 6,6′‐substituted 1,1′‐bi‐2‐naphthol (BINOL) scaffold. The resulting complexes were analysed through a broad variety of NMR spectroscopy experiments, high‐resolution mass spectrometry, CD and UV/Vis spectroscopy, and single‐crystal X‐ray diffraction. As proven by these experiments, the self‐assembly occurs through a completely diastereoselective and narcissistic self‐sorting manner to form homochiral Fe2L3 helicates. The stereochemistry of the metal centres is directed by the axial chirality of the BINOL‐based backbone; the (M)‐configured ligand forms the (Δ,Δ) complex, and the (P)‐configured ligand forms the (Λ,Λ) complex.

show abstract

Section: Resultsmentioning

confidence: 99%

Diastereoselective Formation of Homochiral Helicates through Subcomponent Self‐Assembly

et al. 2017

View full text Add to dashboard Cite

show abstract

“…In this respect, peri ‐xanthenoxanthene (PXX),38, 39 the O‐doped analogue of anthanthrene, can be conceptualized as a building unit for engineering a new class of O‐doped PAHs. Substituted PXX derivatives are characterized by excellent carrier‐transport and injection properties, as well as easy processability, chemical inertness, and high thermal stability 40, 41. Due to these properties, PXX has shown exceptional performance when used as active organic semiconductor in transistors for rollable OLEDs 42, 43.…”

Section: Introductionmentioning

confidence: 99%

“…Due to these properties, PXX has shown exceptional performance when used as active organic semiconductor in transistors for rollable OLEDs 42, 43. In particular, it has been proven that the good performance is triggered by 1) the good charge‐transport properties and 2) the good thermal and chemical stability against parasitic oxidation occurring at the periphery of the π‐ conjugated system 41, 44…”

Section: Introductionmentioning

confidence: 99%

Tailoring Colors by O Annulation of Polycyclic Aromatic Hydrocarbons

Miletić

Fermi

Orfanos

et al. 2017

Chemistry A European J

View full text Add to dashboard Cite

The synthesis of O‐doped polyaromatic hydro‐ carbons in which two polycyclic aromatic hydrocarbon sub units are bridged through one or two O atoms has been achieved. This includes high‐yield ring‐closure key steps that, depending on the reaction conditions, result in the formation of furanyl or pyranopyranyl linkages through intramolecular C−O bond formation. Comprehensive photophysical measurements in solution showed that these compounds have exceptionally high emission yields and tunable absorption properties throughout the UV/Vis spectral region. Electrochemical investigations showed that in all cases O annulation increases the electron‐donor capabilities by raising the HOMO energy level, whereas the LUMO energy level is less affected. Moreover, third‐order nonlinear optical (NLO) measurements on solutions or thin films containing the dyes showed very good values of the second hyperpolarizability. Importantly, poly(methyl methacrylate) films containing the pyranopyranyl derivatives exhibited weak linear absorption and NLO absorption compared to the nonlinearity and NLO refraction, respectively, and thus revealed them to be exceptional organic materials for photonic devices.

show abstract

“…With good charge transfer properties, thermal stability, and chemical stability, these compounds are often used as compositions of pigments, charge transfer complexes, and organic semiconductors in electronic devices. [9][10][11][12][13][14][15] To the best of our knowledge, PXX derivatives have never been used in anti-tumor applications.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Photodynamic Activity of <i>Peri</i>-xanthenoxanthene Derivatives

Chen

Deng

et al. 2019

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

Photodynamic therapy (PDT) is a modern cancer therapy.But it is still difficult to obtain ideal photosensitizers. We synthesized six new peri-xanthenoxanthene derivatives rapidly and efficiently using solid-phase carbon-bath microwave irradiation technology, and investigated their in vitro photodynamic antitumor activity with 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Our results showed that all compounds exhibited extremely low dark cytotoxicity and good phototoxicity against four human cancer cell lines. In particular, compound 3c showed the best in vitro PDT activity against Hela cells and Bel-7402 cells with IC 50 values of 91 and 74 nmol/L, respectively. Its value of 1-octanol/water partition coefficient (log K ow ) was 0.5309, suggesting that it is a promising photosensitizer for PDT due to its low dark cytotoxicity, high phototoxicity, and potential water solubility.

show abstract

Synthesis, Properties, and Structures of Functionalized peri-Xanthenoxanthene

Cited by 47 publications

References 18 publications

Diastereoselective Formation of Homochiral Helicates through Subcomponent Self‐Assembly

Diastereoselective Formation of Homochiral Helicates through Subcomponent Self‐Assembly

Tailoring Colors by O Annulation of Polycyclic Aromatic Hydrocarbons

Synthesis and Photodynamic Activity of <i>Peri</i>-xanthenoxanthene Derivatives

Contact Info

Product

Resources

About