- A facile synthesis of 1,4-dialkoxy-2,5-diiodobenzenes: reaction of dialkoxybenzenes with iodine monochloride in alcoholic solvents
-
A facile synthesis of 1,4-dialkoxy-2,5-diiodobenzenes via diiodination of the corresponding dialkoxybenzenes with iodine monochloride has been developed. Employment of ah alcoholic solvent as a reaction medium is crucial for attaining a high yield; the reaction in a nonalcoholic solvent usually resulted in a poor yield. The diiodobenzene derivatives are useful intermediates in the synthesis of such advanced materiais as soluble phenylenevinylene polymers anal dialkoxy derivatives of 7,7,8,8-tetracyanoquinodimethane.
- Wariishi, Koji,Morishima, Sin-Ichi,Inagaki, Yoshio
-
-
Read Online
- Hg2+ detection by aniline-based conjugated copolymers with high selectivity
-
Conjugated polymers (P1, P1L and P2-P5) constructed by alkynyl-substituted aniline and substituted arene analogs could be synthesized through Pd-catalyzed Sonogashira coupling. The responsive optical properties of poly(2-ethynyl aniline) (P1 and P1L for d
- Yang, Bin,Li, Guangzhao,Zhang, Xu,Shu, Xin,Wang, Anning,Zhu, Xiaoqing,Zhu, Jin
-
-
Read Online
- Triphenylamine and terpyridine-zinc(ii) complex based donor-acceptor soft hybrid as a visible light-driven hydrogen evolution photocatalyst
-
A donor-acceptor coordination polymer (TPA-Zn) was synthesized by Zn(ii)-assisted self-assembly of an in situ generated triphenylamine (TPA) cored tristerpyridine ligand. The polymer absorbs a broad-spectrum of light and exhibits visible light-assisted hydrogen generation (27.1 mmol g-1 over 9 h) from water with 2.9% quantum efficiency at 400 nm. The microscopy images show a mesoscale fibrous morphology and the Brunauer-Emmett-Teller (BET) analysis reveals the porous nature of TPA-Zn (surface area: 234.5 m2 g; d = 6.98 nm), both of which are helpful for substrate diffusion during catalysis. This journal is
- Ghorai, Manas K.,Kar, Kamal K.,Kumar, Manish,Maji, Tapas Kumar,Samanta, Debabrata,Singh, Sugandha,Verma, Parul
-
supporting information
p. 21968 - 21972
(2020/11/11)
-
- New water soluble terphenylene diethynylene fluorophores
-
Inspired by our earlier works on sensors from dendritic phenyleneethynylenes, two new star-shaped water-soluble fluorophores containing terphenylene diethynylene units and anionic carboxylate peripheries are successfully synthesized. The convergent synthesis relies on Sonogashira cross-coupling reactions between tris-(4-ethynylphenyl)amine and the iodophenyleneethynylene branches. All of the compounds are characterized by 1H, 13C NMR, and mass spectrometry. In aqueous solution, the less polar fluorophore 1 shows lower quantum yield than 2 (18 vs 33 %) as a result of hydrophobic induced aggregation. One of these anionic water-soluble fluorophores exhibits a selective fluorescence quenching by Fe3+ ion in phosphate buffer pH 8.
- Vongnam, Kunnigar,Vilaivan, Tirayut,Sukwattanasinitt, Mongkol,Rashatasakhon, Paitoon
-
p. 197 - 202
(2014/03/21)
-
- A helical chiral polymer-based chromo-fluorescence and CD response sensor for selective detection of trivalent cations
-
A novel chiral (S)-BINAM-based fluorescent polymer sensor was designed and synthesized by the polymerization of 4,4′-((2,5-dibutoxy-1,4-phenylene) bis(ethyne-2,1-diyl))-dibenzaldehyde (M-1) with (S)-2,2′-binaphthyldiamine (S-BINAM, M-2) via Schiff's base formation. The resulting helical chiral polymer sensor exhibited remarkable turn-on bright blue fluorescence color upon the addition of trivalent metal ions under a commercially available UV lamp; this change can be clearly observed by the naked eye for direct visual discrimination at low concentration. More importantly, the addition of trivalent metal cations can lead to a most pronounced change of CD spectra of the chiral polymer indicating this kind chiral sensor can also be used as a sole probe for selective recognition of trivalent metal cations based on CD spectra.
- Wang, Lu,Li, Fei,Liu, Xunhua,Wei, Guo,Cheng, Yixiang,Zhu, Chengjian
-
p. 4070 - 4075
(2013/09/23)
-
- Homoleptic "star" Ru(II) polypyridyl complexes: Shielded chromophores to study charge-transfer at the sensitizer-TiO2 interface
-
Three homoleptic star-shaped ruthenium polypyridyl complexes, termed Star YZ1, Star YZ2, and Star YZ3, where the Ru(II) center is coordinated to three bipyridine ligands each carrying two oligo(phenylene ethynylene) (OPE) rigid linker units terminating wi
- Johansson, Patrik G.,Zhang, Yongyi,Meyer, Gerald J.,Galoppini, Elena
-
p. 7947 - 7957
(2013/08/23)
-
- Synthesis, optical and electrochemical properties of novel D-π-A type conjugated polymers based on benzo[c][1,2,5]selenadiazole unit via alkyne module
-
Three novel donor-π-acceptor (D-π-A) type conjugated polymers P-1, P-2, and P-3 based on benzo[c][1,2,5]selenadiazole moiety and phenyl or naphthyl group via alkyne module were firstly prepared by Sonogashira-Hagihara reaction of various diiodo aryl compounds with the key monomer 4,7-diethynylbenzo[c] [1,2,5]selenadiazole (M-1), which was synthesized by a strategy of firstly introducing the trimethylsilylacetylene flexible group, and then introducing the selenium atom. The polymers displayed obvious absorption peaks at the region from 503 to 510 nm and narrow orange-red or red fluorescence in the range of 576-595 nm because benzo[c][1,2,5]selenadiazole unit can effectively reduce the lowest unoccupied molecular orbital (LUMO) energy levels of these polymers. The band gaps of these polymers can be tuned in the range of 1.37-1.76 eV by using different aryl donor groups. These findings indicate that these benzo[c][1,2,5]selenadiazole-based conjugated polymers can be developed for excellent fluorescent materials.
- Li, Duanqin,Li, Hui,Liu, Miaochang,Chen, Jiuxi,Ding, Jinchang,Huang, Xiaobo,Wu, Huayue
-
p. 6158 - 6164
(2013/10/22)
-
- Large stokes shift chiral polymers containing (R,R)-salen-based binuclear boron complex: Synthesis, characterization, and fluorescence properties
-
Two novel chiral fluorescence polymers P-1 and P-2 incorporating (R,R)-salen-based binuclear boron complex in the main chain backbone were synthesized by (R,R)-salen-based boron complex (M-1) with 9,9-dibutyl-2,7- diethynyl-9H-fluorene (M-2) and 1,4-dibutoxy-2,5-diethynylbenzene (M-3) via Pd-catalyzed Sonogashira coupling reaction, respectively. The chiral polymers were characterized by 1H NMR, UV-vis spectroscopy, photoluminescence (PL), gel permeation chromatography (GPC), TGA, DSC, cyclic voltammetry (CV), and theoretical calculation using density-functional theory (DFT) method. P-1 and P-2 show anisotropic fluorescence property with emission spectral maxima at 474 nm and 514 nm, respectively. Both two chiral polymers can exhibit high fluorescence quantum yields (up to 44% and 52%) with large Stokes shifts over 90 nm. The DFT theoretical calculation of the polymer repeating units indicates that the optical band gaps of P-1 is higher than that of P-2, which was consistent with the CV determination results.
- Ma, Xiao,Jiao, Jiemin,Yang, Jing,Huang, Xiaobo,Cheng, Yixiang,Zhu, Chengjian
-
scheme or table
p. 3894 - 3899
(2012/10/18)
-
- In situ Cu(II)-containing chiral polymer complex sensor for enantioselective recognition of phenylglycinol
-
A chiral polymer P1 was synthesized by the polymerization of 2,5-dibutoxy-1,4-di(benzaldehyde)-1,4-diethynylbenzene (M-1) with (R,R)-1,2-diaminocyclohexane (M-2) via Schiff's base formation, and the chiral polymer P2 could be obtained by the reduction reaction of P1 with NaBH 4. P2 can serve as a "turn-off" fluorescent sensor toward Cu2+ and Ni2+. The in situ generated Cu(II)-containing polymer complex of P2 (Cu(II)-P2) can exhibit remarkable "turn-on" fluorescence enhancement response and considerable enantioselectivity toward unmodified phenylglycinol via a ligand displacement mechanism. More importantly, (R,R)-Cu(II)-P2 solution can turn on bright blue fluorescence color change again upon addition of l-phenylglycinol under a commercially available UV lamp, which can be clearly observed by the naked eyes for direct visual discrimination at low concentration. The simple, rapid and sensitive benign process makes this protocol promising for recognition of phenylglycinol enantiomers.
- Wang, Lu,Song, Fengyan,Hou, Jiali,Li, Junfeng,Cheng, Yixiang,Zhu, Chengjian
-
p. 6033 - 6038
(2013/02/25)
-
- Polymer-based fluorescence sensor incorporating triazole moieties for Hg2+ detection via click reaction
-
The polymer could be obtained by the polymerization of 1,4-dibutoxy-2,5-diethynylbenzene (M-1) with 1,4-diazidobenzene (M-2) via click reaction. The polymer show blue fluorescence. The responsive optical properties of the polymer on various transition metal ions were investigated by fluorescence spectra. Compared with other cations, such as Co2+, Ni2+, Ag+, Cd2+, Cu2+ and Zn2+, Hg2+ can exhibit the most pronounced fluorescence response of the polymer Hg2+ can exhibit the most pronounced fluorescence response of the polymer due to triazole moiety in the polymer main chain as the metal binding ligand. The results indicate this kind of conjugated polymer with triazole moiety synthesized by click reaction can be used as a selective fluorescence sensor for Hg2+ detection.
- Huang, Xiaobo,Meng, Jie,Dong, Yu,Cheng, Yixiang,Zhu, Chengjian
-
experimental part
p. 3064 - 3067
(2011/11/12)
-
- A highly selective fluorescence-based polymer sensor incorporating an (R,R)-salen moiety for Zn2+ detection
-
A chiral polymer incorporating an (R,R)-salen moiety was synthesized by the polymerization of (R,R)-1,2-diaminocyclohexane with 2,5-dibutoxy-1,4- di(salicyclaldehyde)-1,4-diethynyl-benzene by a nucleophilic additionelimination reaction. The fluorescence responses of the (R,R)-salen-based polymer toward various metal ions were investigated by fluorescence spectra. Compared with other cations, such as Na+, K+, Mg2+, Ca 2+, Mn2+, Fe2+, Fe3+, Co 2+, Ni2+, Cu2+, Ag+, Cd 2+, Hg2+, and Pb2+, Zn2+ can lead to a pronounced fluorescence enhancement as high as 7.8-fold together with an obvious blue-shift change of the chiral polymer. More importantly, the fluorescent color of the polymer changed to bright blue instead of weak yellow after addition of Zn2+, which can be easily detected by the naked eye. The results indicate that this kind of chiral polymer, incorporating an (R,R)-salen moiety as a receptor in the main chain backbone, can exhibit high sensitivity and selectivity for Zn2+ recognition.
- Xu, Ying,Meng, Jie,Meng, Lingxing,Dong, Yu,Cheng, Yixiang,Zhu, Chengjian
-
scheme or table
p. 12898 - 12903
(2011/02/23)
-
- Double helices with a controlled helicity composed of biphenol-derived phosphoric acid diesters
-
A new modular strategy to build artificial double helical oligomers and polymers with a controlled helicity composed of biphenol-derived phosphoric acid diesters through amidinium-carboxylate salt bridges was reported. The biphenyl derivative was dimerized as a linker and the dimer product was treated with phosphoryl chloride after hydrolysis of the acetoxy groups to afford the optically active phosphoric acid diesters. The calculated results show that the structure of homo-duplex of (S)-1 reveals a double-stranded helical structure, in which two aromatic rings of the linker moieties overlap with each other. The compound is also found to exhibit induced circular dichroism (ICD) in the π-conjugated chromophore regions above 300 nm. Optically active substituents introduced on the phenylene linker unit contribute to the bias in an excess of one helical sense.
- Yamada, Hidekazu,Maeda, Katsuhiro,Yashima, Eiji
-
supporting information; experimental part
p. 6794 - 6798
(2010/02/28)
-
- Synthesis and anion-selective complexation of cyclophane-based cyclic thioureas
-
Cyclic thiourea derivatives having three different types of cyclophane structure, ortho-meta, meta-meta, and meta-para, and a lariat-type thiourea, were synthesized, and their anion-binding ability was examined. The association constants for the complexation between the receptors and several anions in DMSO-d6 were measured by the titration method using 1H NMR spectroscopy. All receptors, except for the meta-para cyclophane, exhibit selective binding to the dihydrogenphosphate anion, which is stronger than that of the acyclic reference compound. The lariat-type receptor binds anions even more strongly than the cyclic receptors which do not possess the third binding site.
- Sasaki, Shin-ichi,Mizuno, Masaaki,Naemura, Koichiro,Tobe, Yoshito
-
p. 275 - 283
(2007/10/03)
-
- The preparations and some properties of mixed aryl-thienyl oligomers and polymers
-
The syntheses by transition metal coupling reactions of a large number of oligomers constructed from benzene and thiophene rings are described. The first use of arylcadmium chlorides for such coupling reactions is reported. The routes chosen allow for rational variation in the modes of linkage, the substitution and the proportions of the two units. The benzene and thiophene rings are always joined in a known order and may bear a wide variety of regularly spaced functional groups. Additionally the shape of the oligomers may be varied at will. In all cases p-type doping with iodine or ferric chloride leads to large enhancements in conductivity.
- Pelter, Andrew,Jenkins, Ieuan,Jones, D. Elfyn
-
p. 10357 - 10400
(2007/10/03)
-
- Fluorescence Studies of Poly(p-phenyleneethynylene)s: The Effect of Anthracene Substitution
-
The poly(p-phenyleneethynylene) molecules, PI-PIII, synthesized by a palladium-catalyzed cross-coupling reaction of diiodobenzene derivatives and derivatives of 1,4-diethynylbenzene, are highly luminescent materials.The polymers are soluble by virtue of the -OC16H33 groups introduced on the aromatic rings and by controlling their molecular weight.The fluorescent quantum yields are between 0.35 and 0.40 depending on the material.The excited-state lifetimes of the polymers are 1-2 ns, slightly shorter than that of the model compund, 1,4-diphenylethynyl-2,5-dibutoxybenzene, which has a lifetime of 3 ns.Incorporation of anthracene, coupled at the 9,10-positions by using 9,10-dibromoanthracene, into the polymer backbone decreases the quantum yield to between 0.05 and 0.27 depending on the anthracene content.In addition, low-energy electronic transitions and longer wavelength emission bands associated with the anthracene group are produced.The polymers harvest optical energy and transfer it to the anthracene resulting in emission from this chromophore.In the case where only terminal anthracene units, introduced by using 9-bromo-10-phenylethynylanthracene, are present, the process is very efficient with >95percent of the energy being transferred to the end groups.
- Swager, Timothy M.,Gil, Caroline J.,Wrighton, Mark S.
-
p. 4886 - 4893
(2007/10/02)
-