- A C3-symmetric macrocycle-based, hydrogen-bonded, multiporous hexagonal network as a motif of porous molecular crystals
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A C3-symmetric π-conjugated macrocycle combined with an appropriate hydrogen bonding module (phenylene triangle) allowed the construction of crystalline supramolecular frameworks with a cavity volume of up to 58%. The frameworks were obtained t
- Hisaki, Ichiro,Nakagawa, Shoichi,Tohnai, Norimitsu,Miyata, Mikiji
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- Novel octabromo-substituted lanthanide(III) phthalocyanines – Prospective compounds for nonlinear optics
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Novel octabromo-substituted lanthanide(III) phthalocyanines were obtained via template method starting from corresponding 4,5-dibromophthalonitrile and identified by high-resolution mass-spectrometry, 1H nuclear magnetic resonanse and infra red spectroscopy. To achieve an initial 4,5-dibromophthalonitrile the reaction conditions of Pd(0) catalyzed cyanation were optimized. The peripheral bromine atoms impact on the optical properties of phthalocyanine complexes. The bathochromic shift of the main absorption band (Q band) was observed going from unsubstituted to octachloro- and then to octabromo-substituted phthalocyanines. All complexes demonstrated nonlinear optical responses in the DMF solution. Increasing the intensity of laser radiation leads to a nonlinear decrease in transmittance and further restoration of optical properties when switching back to linear mode. Nonlinear optical responses depend on the central ion nature. Europium phthalocyanine showed the enhanced nonlinear absorption coefficient compared to lutetium and terbium complexes. This was caused by an enhanced population of excited state and faster excitement for complexes with large central ions. The impact of peripheral bromine groups into nonlinear optical properties was determined through the comparison with unsubstituted analogues.
- Borisova, Nataliya E.,Dubinina, Tatiana V.,Gerasimenko, Alexander Yu.,Kuzmina, Elena A.,Saveliev, Mikhail S.,Tomilova, Larisa G.,Vasilevsky, Pavel N.
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- Polymorphism of 2D Imine Covalent Organic Frameworks
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We designed and synthesized A2B2 type tetraphenyl benzene monomers (p-, m-, and o-TetPB) which have the para-, meta, and ortho-substituted isomeric structures, for the direct construction of isomeric frameworks. Interestingly, both kagome (kgm) and monoclinic square (sql) framework isomers are produced from either p-TetPB (C2h symmetry) or m-TetPB (C2v symmetry) by changing reaction solvents, while their isomeric structures are characterized by X-ray diffraction, computational simulation, microscopy, and sorption isotherm measurements. Only sql frameworks was formed for o-TetPB (C2v symmetry), irrespective of reaction solvents. These results disclose a unique feature in the framework structural formation, that is, the geometry of monomers directs and dominates the lattice growth process while the solvent plays a role in the perturbation of chain growth pattern. The isomeric frameworks exhibit highly selective adsorption of vitamin B12 owing to pore shape and size differences.
- Li, Yusen,Guo, Linshuo,Lv, Yongkang,Zhao, Ziqiang,Ma, Yanhang,Chen, Weihua,Xing, Guolong,Jiang, Donglin,Chen, Long
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supporting information
p. 5363 - 5369
(2021/01/20)
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- Discrete Platinum(II) Metallacycles with Inner- and Outer-Modified 9,10-Distyrylanthracene: Design, Self-Assembly, and Luminescence Properties
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To completely unravel the relationship between structures and luminescence properties of inner- and outer-modified metallacycles, two rhombic metallacycles S1 and S2 with 9,10-distyrylanthracene (DSA) were constructed herein via the design of DSA moieties on the inside or outside of metallacycles. Similar building blocks of the two metallacycles led to the same emission wavelengths in a dilute solution. In contrast, their fluorescence emissions in the aggregation and solid states were significantly different and revealed interesting emission behaviors from structures with inner- and outer-modified design. Finally, based on their luminescence properties, a tunable solid-state fluorescence emissive material was easily obtained by the mixing of two supramolecules in different ratios. This unique design suggested that the modified position of fluorophores exerts a key impact on the adjustment of luminescence from a dilute solution to the aggregated state and will be of great significance for the development of luminescent materials based on supramolecules.
- Li, Meng,Pan, Guocui,Shi, Junjuan,Tian, Wenjing,Tong, Hui,Wang, Ming,Xu, Bin,Yu, Hao
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supporting information
(2022/03/27)
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- A novel modular approach to triazole-functionalized phthalocyanines using click chemistry
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(Chemical Equation Presented) A novel, elegant, and significantly improved protocol for the synthesis of a protected octaacetylene phthalocyanine is described. Inexpensive, mild, and environmentally benign iodination of 1,2-dibromobenzene and subsequent optimized chemoselective palladium-catalyzed cyanation are employed to effectively build up the key intermediate 4,5-dibromophthalonitrile in two steps. Introduction of the tert- butyldimethylsilyl-protected acetylene moieties via a Sonogashira cross-coupling provides the desired phthalonitrile precursor that, after cyclization, yielded the protected octaacetylene phthalocyanine. Subsequently, in situ deprotection and "clicking" are employed as a highly efficient and quantitative route to a novel class of octatriazole-functionalized phthalocyanines. The ability of such triazole-derived phthalocyanines to form well-defined supramolecular structures upon doping with zinc(II) triflate is demonstrated.
- Jurí?ek, Michal,Kouwer, Paul H. J.,Rehák, Juraj,Sly, Joseph,Rowan, Alan E.
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supporting information; experimental part
p. 21 - 25
(2009/04/07)
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- HETEROACENE DERIVATIVE, TETRAHALOTERPHENYL DERIVATIVE, AND THEIR PRODUCTION METHODS
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There are provided a heteroacene derivative having an excellent oxidation resistance and capable of forming a semiconductor active phase by a coating process, and an oxidation-resistant organic semiconductor material using the same, as well as an organic thin film. [Means for Resolution] heteroacene derivative represented by the formula (1) is obtained by tetrametalation of a tetrahaloterphenyl derivative with a metalation agent and subsequent treatment of the resulting compound with reaction agents: wherein the substituents R1 to R4 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, an aryl group having 4 to 30 carbon atoms, an alkyl group having 3 to 20 carbon atoms, or a halogenated alkyl group having 1 to 20 carbon atoms; T1 and T2 are the same or different and each represents sulfur, selenium, tellurium, oxygen, phosphorus, boron, or aluminum; 1 and m each is an integer of 0 or 1; and rings A and B are the same or different and each has a structure represented by the following formulae (A-1) or (A-2).
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Page/Page column 24
(2019/07/30)
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- TERPHENYLENE DERIVATIVES, TETRAHALOTERPHENYL DERIVATIVES AND PROCESSES FOR THE PRODUCTION OF BOTH
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The invention provides terphenylene derivatives which have excellent oxidation resistance and permit the formation of semiconductor active phases by coating; and oxidation-resistant organic semiconductor materials and organic thin films, made by using the same. The invention relates to production of terphenylene derivatives represented by the general formula (1) by tetralithiating a tetrahaloterphenyl derivative with a lithiating agent and then treating the obtained compound with a copper compound: (1) wherein R1 to R14 are each independently hydrogen, fluoro, chloro, aryl having 4 to 30 carbon atoms, alkynyl having 3 to 20 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkyl having 1 to 20 carbon atoms, halogenated alkyl having 1 to 20 carbon atoms, or diarylamino having 8 to 30 carbon atoms; and l, m, and n are each an integer of 0 or 1.
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Page/Page column 61
(2008/06/13)
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