- Triggered emission for rapid detection of hydrogen sulfide chaperoned by large Stokes shift
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Current manuscript demonstrates the development of a reaction-based “turn-on” green emissive molecular probe (P4) for rapid detection of H2S in physiological condition. The probe was found to exhibit low limit of detection (1.19 μM), along with high selectivity, large Stokes shift and good quantum efficiency. The change in the optical behaviour of the probe was also theoretically scrutinized employing density functional theory calculations which stand in the strong agreement with the photophysical outcomes. Given the demand for large Stokes dyes for sensing applications mainly because of their special photophysical properties, and as the reported number is very limited, the present probe with 110 nm Stokes shift is a good addition in the area of large Stokes dyes for H2S recognition in physiological conditions.
- Biswas, Bidisha,Venkateswarulu,Gaur, Pankaj,Sharma, Yamini,Sinha, Sougata,Ghosh, Subrata
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Read Online
- A supramolecular approach of modified polyoxometalate polymerization and visualization of a single polymer chain
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An anthracene modified Anderson-Evans polyoxometalate was polymerized via supramolecular inclusion and then covalent coupling with the support of γ-cyclodextrin (γ-CD) under UV light irradiation. The formed main chain polymers of the inorganic polyanions self-assembled into fibrous bundles and single-strand chains were visualized and characterized via TEM and other techniques.
- Guan, Weiming,Wang, Gengxin,Ding, Jingbo,Li, Bao,Wu, Lixin
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Read Online
- Selective Carbon-Carbon Bond Amination with Redox-Active Aminating Reagents: A Direct Approach to Anilines?
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Amines are among the most fundamental motifs in chemical synthesis, and the introduction of amine building blocks via selective C—C bond cleavage allows the construction of nitrogen compounds from simple hydrocarbons through direct skeleton modification. Herein, we report a novel method for the preparation of anilines from alkylarenes via Schmidt-type rearrangement using redox-active amination reagents, which are easily prepared from hydroxylamine. Primary amines and secondary amines were prepared from corresponding alkylarenes or benzyl alcohols under mild conditions. Good compatibility and valuable applications of the transformation were also displayed.
- Qiu, Xu,Wang, Yachong,Su, Lingyu,Jin, Rui,Song, Song,Qin, Qixue,Li, Junhua,Zong, Baoning,Jiao, Ning
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supporting information
p. 3011 - 3016
(2021/09/13)
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- Inducing apoptosis through upregulation of p53: structure–activity exploration of anthraquinone analogs
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We previously reported a series of p53-elevating anthraquinone compounds with considerable cytotoxicity for acute lymphoblastic leukemia (ALL) cells. To further develop this class of compounds, we examined the effect of a few key structural features on the anticancer structure–activity relationship (SAR) in ALL cells. The active analogs showed comparable cytotoxicity and upregulation of p53 but did not induce significant downregulation of MDM2 as seen with the lead compound AQ-101, indicating the importance of the anthraquinone core scaffold for MDM2 regulation. The result from the current study not only contributes to the SAR framework of these anthraquinone derivatives but also opens up new chemical space for further optimization work.
- Agbowuro, Ayodeji A.,Anifowose, Abiodun,Lu, Wen,Tan, Chalet,Tripathi, Ravi,Wang, Binghe,Yang, Xiaoxiao
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p. 1199 - 1210
(2020/06/17)
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- Synthesis, Structure and Properties of Fused π-Extended Acridone Derivatives
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Benzene- and naphthalene-fused acridone derivatives with hexyl and phenyl groups at the amino position were synthesized and their properties were investigated experimentally and computationally. All the structures of these fused π-extended acridone derivatives were unambiguously confirmed by single-crystal X-ray analysis, which revealed the presence of face-to-face π–π stackings along the acridone moiety and the intermolecular hydrogen bond-directed molecular packings of the phenyl-substituted acridone derivatives in the crystals. Moreover, the dimerization of linearly fused acridone derivative was observed after storing the crystals over months. The benzene ring at the turning point of the angularly fused acridone derivatives contained relatively longer and shorter C–C bonds, which affected the molecular conjugation, as confirmed by the results of photophysical characterization and the study of the aromaticity. Mobility calculations based on the molecular packings in the single crystals showed that the linearly fused acridone derivatives bearing better electron and hole mobilities are good candidates of organic functional materials.
- Gao, Hongshuai,Zhang, Gang
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supporting information
(2020/08/26)
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- Photoactivated Healable Vitrimeric Copolymers
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A composite polymer based on vinylogous urethane vitrimer bonding with both photodimerizable and thermally exchangeable functionalities is described. Polymers containing various ratios of photodimerizable diaminoanthracene monomers and thermally exchangeable diaminoalkyl monomers linked by a common bisacetoacetate group are studied. It is demonstrated that alkyl amines undergo the necessary thermal exchange reactions for vinylogous urethane vitrimers, while aromatic amines do not. UV-induced dimerization of the anthracene units results in changes to the rheological properties and the glass transition temperature due to polymer cross-linking. Rapid and near-complete scratch healing upon heating is demonstrated, with a tunable onset temperature for healing controlled by UV irradiation. The viability of a composite vitrimeric system, wherein vitrimeric monomers are combined with non-vitrimeric, stimuli-responsive monomers to generate random copolymers with new properties, is demonstrated.
- Wright, Taylor,Tomkovic, Tanja,Hatzikiriakos, Savvas G.,Wolf, Michael O.
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- Synthesis of Anthradan analogues by regioselective Friedel-Crafts reactions on N,N-dihexylanthracen-2-amine
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An efficient synthetic route using a Friedel-Crafts acylation approach was developed to obtain fluorophores such as 1-(6-(dihexylamino)anthracen-1-yl) propan-1-one (1b) and 1-(7-(dihexylamino)anthracen-1-yl)propan-1-one (1c) with a push-pull electronic conjugation starting from 2-aminoanthracene-9,10-dione (4). These compounds are analogues of 1-(6-(dihexylamino)anthracen-2-yl)propan- 1-one (Anthradan) and they exhibit the same additional redshift emission and absorption spectra. Furthermore, we have synthesized other derivatives of Anthradan via the Friedel-Crafts approach in good yields.
- De Miranda, Maicon G.,De Oliveira, Matheus F.G.,Lopes, Rosangela S.C.,Da Silva, Antonio J.R.,Albert, André L.M.,Lopes, Claudio C.
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supporting information
p. 2587 - 2590
(2013/06/26)
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- Kinetics of hydrogen bonding between anthracene urea derivatives and anions in the excited state
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Urea compounds are useful anion sensors due to their hydrogen-bonding capabilities. We investigated the emissive properties of complexes consisting of urea-anthracene (nPUA, n = 1, 2) host compounds and acetate anions held as guests through intermolecular hydrogen bonding. The kinetics of a new emission band formed by conformational changes in the excited singlet state were revealed. The new band is thought to arise from a charge-transfer interaction between the anthracene and urea moieties after intermolecular hydrogen-bond reconfiguration in the excited state, with rate constants of 2.4 × 10 9 and 4.0 × 107 s-1 for 1PUA and 2PUA, respectively.
- Ikedu, Satomi,Nishimura, Yoshinobu,Arai, Tatsuo
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experimental part
p. 8227 - 8233
(2011/09/20)
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- Direct synthesis of amino-substituted aromatic phosphonates via palladium-catalyzed coupling of aromatic mono-and dibromides with diethyl phosphite
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An efficient Pd-catalyzed carbon-phosphorus bond-forming route is described for the direct synthesis of diethyl arylphosphonates bearing amino and alkylamino groups on the aromatic ring. Copyright
- Bessmertnykh, Alla,Douaihy, Christiane Morkos,Guilard, Roger
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supporting information; experimental part
p. 738 - 739
(2011/04/21)
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- Preparation and cyclization of some N-(2,2-Dimethylpropargyl) homo- And heteroaromatic amines and the synthesis of some pyrido[2,3-d]pyrimidines
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The Cu(I) catalyzed cyclization of o-substituted N-(2,2-dimethylpropargyl) anilines yields 8-substituted 2,2-dimethyl-1,2-dihydroquinolines, while m-substituted analogues provide a mixture of 5- and 7-substituted dihydroquinoline systems. This reaction can be extended to 2-amino-N-(2,2- dimethylpropargyl)anthracene, yielding a dihydronaphtho[2,3-f]quinoline product, and to aminoquinoline derivatives, which yield substituted phenanthroline products. Pyridine analogues did not cyclize, apparently because of complexation with the copper reagent. An alternative synthetic approach to these cyclized products, when complexation may be a problem, is illustrated by the following example. 2-Chloro-4-N-(2,2-dimethylpropargyl)pyrimidine was reduced using a Lindlar catalyst to the corresponding alkene which did not undergo an amino-Claisen rearrangement. However, the 5-bromopyrimidine alkene analogue underwent addition with phenylselanyl bromide to give a product that cyclized, using butyllithium, to a pyrido[2,3-d]pyrimidine selenium-containing product from which the selenium moiety could be removed to yield either a dihydro- or a tetrahydro-pyrido[2,3-d]pyrimidine system. A Heck reaction on the 5-bromopyrimidine alkene gave a 5-methylene-6,7-dihydro-5H-pyrrolo[2,3-d] pyrimidine. CSIRO 2005.
- Holman, Michelle A.,Williamson, Natalie M.,Ward, A. David
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p. 368 - 374
(2007/10/03)
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- Effects of Substituents and Solvents on the Electronic Spectra of 9,10-Dihydro-9,10-o-benzenoanthracene-1,4-diones: Intramolecular Charge Transfer
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Electronic spectra of substituted 9,10-dihydro-9,10-o-benzenoanthracene-1,4-diones (triptycenequinones) in various solvents and that of benzo- and dibenzotriptycenequinones were investigated in this paper.Intramolecular charge-transfer (CT) bands were observed in triptycenequinone system as a result of intramolecular interaction between benzene ring and benzoquinone moiety.Substituents on the benzene rings strongly affected the CT bands.Electron-donating groups gave absorption maxima at long wavelength.Naphthalene ring gave similar but stronger CT bands than benzene ring.Hammett ?+ value of substituents gave good linear relationship with the energy of the CT bands.Calculations of reduced charge matrix of triptycenequinones by extended Hueckel theory showed the charge of aromatic ring(s) were transferred to benzoquinone moiety accompanying HOMO-LUMO excitation.Especially, absorption maxima of the methyl-substituted triptycenequinones gave good correlation with the amounts of charge transferred from benzene ring to benzoquinone moiety.These analysis confirmed clearly CT character of the absorption maxima of triptycenequinones.However, solvent effect of these CT bands maxima is not so clear as the substituent effect.
- Kitaguchi, Nobuya
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p. 800 - 807
(2007/10/02)
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- PHOTOACTIVABLE FLUOROPHORES. 1. SYNTHESIS AND PHOTOACTIVATION OF o-NITROBENZYL-QUENCHED FLUORESCENT CARBAMATES
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The synthesis and photoactivation of a new type of fluorescent probe, the photoactivable fluorophore (PAF) are described.The PAFs described in this paper consist of fluorescent aromatic amines coupled to substituted nitrobenzyl quenching chromophores via a carbamate linkage.Photoactivation occurs by an intramolecular photo-redox reaction, converting the o-nitrosobenzaldehyde hemiacetal which fragments with loss of CO2 to liberate the fluorescent amine.Photoactivation quantum yields also are reported.
- Cummings, Richard T,Krafft, Grant A.
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- PHOTOCHEMICAL DECOMPOSITION OF 2-AZIDOPHENAZINE IN ALCOHOLS AND IN THE PRESENCE OF CYANIDE ION
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The photochemical decomposition of 2-azidophenazine in alcoholic solvents has been investigated. 1-Amino-2-alkoxyphenazines are formed in neutral and (in higher yield and together with 2-amino-1-chlorophenazine) in acidic conditions, while the azepinoquinoxaline 7 is formed in basic conditions.With cyanide ion nucleophilic attack takes place giving 1-amino-2-phenazine carbonitrile.To allow comparison, 2-azidonaphthalene, 2-azidoanthracene and 2-azidoanthraquinone have also been photodecomposed in the conditions in which the most interesting results are obtained from 2-azidophenazine.The mechanism of these reactions is briefly discussed.
- Albini, Angelo,Bettinetti, Gian Franco,Fasani, Elisa,Pietra, Silvio
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