104-36-9Relevant academic research and scientific papers
Polymer-based fluorescence sensor incorporating triazole moieties for Hg2+ detection via click reaction
Huang, Xiaobo,Meng, Jie,Dong, Yu,Cheng, Yixiang,Zhu, Chengjian
, p. 3064 - 3067 (2010)
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.
In situ Cu(II)-containing chiral polymer complex sensor for enantioselective recognition of phenylglycinol
Wang, Lu,Song, Fengyan,Hou, Jiali,Li, Junfeng,Cheng, Yixiang,Zhu, Chengjian
, p. 6033 - 6038 (2012)
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.
Two polymorphs and cocrystal of styryl-pyridine derivatives with tuned emission induced by Co2+ and Zn(phen)32+
Zhang, Ruilong,Zhang, Qiong,Liu, Zhaodi,Yang, Longmei,Wu, Jieying,Zhou, Hongping,Yang, Jiaxiang,Tian, Yupeng
, p. 2039 - 2044 (2014)
A styryl-pyridine derivative, 2,5-dibutoxy-1,4-bis[2-(4-pyridyl)ethenyl] benzene (L), has been designed and synthesised. Two polymorphs of L and crystals of [Zn(phen)3]2L(ClO4)4 were obtained by different crystallisation conditions. Polymorph-α was prepared by a solvent evaporation method. However, polymorph-β and a cocrystal of [Zn(phen)3]2L(ClO4)4 were obtained by different inducing reagents. It has been found that there are, in total, four independent conformations of the molecule L in the three kinds of crystals. We have calculated the standard molar enthalpy of formation (ΔHm) of each conformation and demonstrated that the stabilisation energy of each conformation significantly relies on both the planarity of the molecules (L) and bond length of conjugated bridges. Furthermore, the photophysical properties of the three kinds of crystals also exhibit differences in the vibration and absorption spectroscopies, solid-state photoluminescence and time-resolved fluorescence, which may arise from the chromophore's stacking modes and the intermolecular electronic interactions in the crystals. These results revealed that the optical properties of functional organic materials could be tuned by controlling their crystallisation environment for a specific molecule. The Royal Society of Chemistry 2014.
Triphenylamine and terpyridine-zinc(ii) complex based donor-acceptor soft hybrid as a visible light-driven hydrogen evolution photocatalyst
Ghorai, Manas K.,Kar, Kamal K.,Kumar, Manish,Maji, Tapas Kumar,Samanta, Debabrata,Singh, Sugandha,Verma, Parul
, p. 21968 - 21972 (2020)
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
Fluorescent bispyrroles. New building blocks for novel π-conjugated polymers
Eldo,Arunkumar,Ajayaghosh
, p. 6241 - 6244 (2000)
Several bispyrroles which are bridged through conjugated aromatic moieties were synthesized by the Wittig-Horner-Emmons reaction. Photophysical and electrochemical data of these highly fluorescent monomers reveal that they are useful building blocks for the design of a wide variety of novel π-conjugated polymers, which may find application as potential optoelectronic materials. (C) 2000 Elsevier Science Ltd.
Direct evidence for secondary interactions in planar and nonplanar aromatic π-conjugates and their photophysical characteristics in solid-state assemblies
Goel, Mahima,Narasimha, Karnati,Jayakannan, Manickam
, p. 5102 - 5112 (2015)
Direct evidence for non-covalent secondary interactions in planar and nonplanar aromatic π-conjugates and their solid-state assemblies is established. A series of horizontally, vertically, and radially expanded oligo(phenylenevinylene)s (H-OPVs, V-OPVs, and R-OPVs, respectively) were designed with a fixed π-core and variable alkyl chain lengths on the periphery. Single-crystal structures of the OPVs were resolved to trace the secondary interactions that direct the solid-state self-organization and molecular packing of the chromophores. The H-OPVs were found to be planar, and they did not show any secondary interactions in the crystal lattices. The V-OPVs and R-OPVs were found to be nonplanar and to exhibit multiple CH/π hydrogen-bonding interactions among aryl hydrogen donors and acceptors. The enthalpies of the melting and crystallization transitions revealed that the planar H-OPVs are highly crystalline compared with the nonplanar R-OPVs and V-OPVs. Polarized light microscopy studies revealed the formation of one-dimensional nematic mesophases in H-OPVs. The absolute solid-state photoluminescence quantum yields (PLQYs) of the OPVs were determined using an integrating sphere setup. The highly packed H-OPVs showed low PLQYs compared with those of the weakly packed V-OPVs and R-OPVs. Time-resolved fluorescence decay measurements revealed that the excited-state decay dynamics of highly packed H-OPVs was much faster with respect to their low PLQYs. The decay profiles were found to be relatively slow (with higher life time (τ)) in the V-OPVs and R-OPVs. A field-effect transistor (FET) device was constructed for an OPV sample that showed a hole carrier mobility in the range of 10-5 cm2 V-1 s-1. The present investigation thus provides a new opportunity to trace the role of secondary interactions on π-conjugated mesophase self-assemblies and their solid-state emission and FET devices, more specifically based on OPV chromophores.
Solvent-free synthesis of pillar[6]arenes
Santra,Kopchuk,Kovalev,Zyryanov,Majee,Charushin,Chupakhin
, p. 423 - 426 (2016)
An efficient solvent-free procedure for the synthesis of pillar[6]arenes has been developed. The procedure involves the solid-state condensation of finely milled 1,4-dialkoxybenzene and paraformaldehyde by grinding in the presence of a catalytic amount of H2SO4. The use of organic solvents for the extraction of products has also been avoided. Operational simplicity, compatibility with various 1,4-dialkoxybenzenes, non-chromatographic purification technique, high yields and mild reaction conditions are the notable advantages of this procedure. A large scale reaction demonstrated the practical applicability of this methodology.
Large stokes shift chiral polymers containing (R,R)-salen-based binuclear boron complex: Synthesis, characterization, and fluorescence properties
Ma, Xiao,Jiao, Jiemin,Yang, Jing,Huang, Xiaobo,Cheng, Yixiang,Zhu, Chengjian
, p. 3894 - 3899 (2012)
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.
Protein Adsorption Switch Constructed by a Pillar[5]arene-Based Host-Guest Interaction
Xiao, Xuan,Nie, Guanrong,Zhang, Xiaoyan,Tian, Demei,Li, Haibing
, p. 941 - 945 (2016)
The interfacial properties of solid substrates are of importance for protein adsorption. Herein, we report a reversible protein adsorption switch based on the host-guest interaction of the butoxy pillar[5]arene and adipic acid. By the detector of the contact angle (CA), atomic force microscopy (AFM), and luminoscope on the silicon substrate, the intelligent protein switch exhibits excellent adsorptivity for BSA and switch performance by pH regulation.
Humidity Sensing through Reversible Isomerization of a Covalent Organic Framework
Jhulki, Samik,Evans, Austin M.,Hao, Xue-Li,Cooper, Matthew W.,Feriante, Cameron H.,Leisen, Johannes,Li, Hong,Lam, David,Hersam, Mark C.,Barlow, Stephen,Brédas, Jean-Luc,Dichtel, William R.,Marder, Seth R.
, p. 783 - 791 (2020)
Here we report that a covalent organic framework (COF), which contains 2,5-di(imine)-substituted 1,4-dihydroxybenzene (diiminol) moieties, undergoes color changes in the presence of solvents or solvent vapor that are rapid, passive, reversible, and easily detectable by the naked eye. A new visible absorption band appears in the presence of polar solvents, especially water, suggesting reversible conversion to another species. This reversibility is attributed to the ability of the diiminol to rapidly tautomerize to an iminol/cis-ketoenamine and its inability to doubly tautomerize to a diketoenamine. Density functional theory (DFT) calculations suggest similar energies for the two tautomers in the presence of water, but the diiminol is much more stable in its absence. Time-dependent DFT calculations confirm that the iminol/cis-ketoenamine absorbs at longer wavelength than the diiminol and indicate that this absorption has significant charge-transfer character. A colorimetric humidity sensing device constructed from an oriented thin film of the COF responded quickly to water vapor and was stable for months. These results suggest that tautomerization-induced electronic structure changes can be exploited in COF platforms to give rapid, reversible sensing in systems that exhibit long-term stability.
