19057-50-2Relevant articles and documents
Highly Efficient and Reversible Iodine Capture in Hexaphenylbenzene-Based Conjugated Microporous Polymers
Liao, Yaozu,Weber, Jens,Mills, Benjamin M.,Ren, Zihao,Faul, Charl F. J.
, p. 6322 - 6333 (2016)
The effective and safe capture and storage of radioactive iodine (129I or 131I) is of significant importance during nuclear waste storage and nuclear energy generation. Here we present detailed evidence of highly efficient and reversible iodine capture in hexaphenylbenzene-based conjugated microporous polymers (HCMPs), synthesized via Buchwald-Hartwig (BH) cross-coupling of a hexakis(4-bromophenyl)benzene (HBB) core and aryl diamine linkers. The HCMPs present moderate surface areas up to 430 m2 g-1, with narrow pore size distribution and uniform ultramicropore sizes of less than 1 nm. Porous properties are controlled by the strut lengths and rigidities of linkers, while porosity and uptake properties can be tuned by changing the oxidation state of the HCMPs. The presence of a high number of amine functional groups combined with microporosity provides the HCMPs with extremely high iodine affinity with uptake capacities up to 336 wt %, which is to the best of our knowledge the highest reported to date. Two ways to release the adsorbed iodine were explored: either slow release into ethanol or quick release upon heating (with a high degree of control). Spectral studies indicate that the combination of microporosity, amine functionality, and abundant π-electrons ensured well-defined host-guest interactions and controlled uptake of iodine. In addition, the HCMPs could be recycled while maintaining 90% iodine uptake capacity (up to 295%). We envisage wider application of these materials in the facile uptake and removal of unwanted oxidants from the environment.
Highly Stable Spherical Metallo-Capsule from a Branched Hexapodal Terpyridine and Its Self-Assembled Berry-type Nanostructure
Chen, Mingzhao,Wang, Jun,Liu, Die,Jiang, Zhilong,Liu, Qianqian,Wu, Tun,Liu, Haisheng,Yu, Weidong,Yan, Jun,Wang, Pingshan
, p. 2555 - 2561 (2018)
Discrete spherical metallo-organic capsules at the nanometer scale, especially those constructed from unique building blocks, have received significant attention recently because of their fascinating molecular aesthetics and potential applications due to their compact cavities. Here, the synthesis and characterization of a hexapodal, branched terpyridine ligand are presented along with the nearly quantitative self-assembly of the resulting tetrameric metallo-nanosphere. This metallo-nanosphere exhibited four quasi-triangular and six rhombus-like facets, all of which were made by the same hook-like bis-terpyridine. Collision-induced dissociation experiments were done to investigate overall stability. The metallo-architecture and host-guest chemistry were investigated with coronene and fully characterized by 1D and 2D NMR, ESI-MS, and transmission electron microscopy. Furthermore, this metallo-nanosphere was observed to hierarchically self-assemble into berry-type structures in an acetonitrile/methanol mixture, by virtue of counterion-mediated attractions. The functional molecular metallo-nanosphere presented here expands the reach of terpyridine coordination systems into molecular containers and other model systems.
The Versatile Synthesis and Self-Assembly of Star-Type Hexabenzocoronenes
Wu, Jishan,Watson, Mark D.,Muellen, Klaus
, p. 5329 - 5333 (2003)
An insoluble disclike building block hexa(4-iodophenyl)-peri-hexabenzocoronene (see picture) was synthesized in an efficient way, and subsequent functionalization led to a series of soluble, star-type hexabenzocoronenes (HBCs), all showing remarkable self-assembly behavior: 1) highly ordered liquid-crystalline materials, 2) dendronized HBCs, and 3) triarylamine-substituted HBCs.
Engineering hydrogen-bonded molecular crystals built from derivatives of hexaphenylbenzene and related compounds
Maly, Kenneth E.,Gagnon, Eric,Maris, Thierry,Wuest, James D.
, p. 4306 - 4322 (2007)
Hexakis[4-(2,4-diamino-1,3,5-triazin-6-yl)phenyl]benzene (4) incorporates a disc-shaped hexaphenylbenzene core and six peripheral diaminotriazine groups that can engage in hydrogen bonding according to established motifs. Under all conditions examined, compound 4 crystallizes as planned to give closely related noninterpenetrated three-dimensional networks built from sheets in which each molecule has six hydrogen-bonded neighbors. In the structure of compound 4, the number of hydrogen bonds per molecule and the percentage of volume accessible to guests approach the highest values so far observed in molecular networks. Analogue 5 (which has the same hexaphenylbenzene core but only four diaminotriazine groups at the 1,2,4,5-positions) and analogue 7 (in which the two unsubstituted phenyl groups of compound 5 are replaced by methyl groups) crystallize according to a closely similar pattern. Analogues with flatter pentaphenylbenzene or tetraphenylbenzene cores crystallize differently, underscoring the importance of maintaining a consistent molecular shape in attempts to engineer crystals with predetermined properties.
7-Azaindolyl- and 2,2′-dipyridylamino-functionalized molecular stars with sixfold symmetry: Self-assembly, luminescence, and coordination compounds
Jia, Wen-Li,Wang, Rui-Yao,Song, Datong,Ball, Steven J.,McLean, Alastair B.,Wang, Suning
, p. 832 - 842 (2005)
Two novel star molecules functionalized with 7-azaindolyl and 2,2′-dipyridylamino groups have been synthesized. Both molecules possess a sixfold rotation symmetry. Molecule L1 is based on the hexaphenylbenzene core with the formula of hexa[p-(7-azaindolyl)phenyl]benzene, while molecule L2 is based on the hexakis(biphenyl)benzene core with the formula of hexa[p-(2,2′-dipyridylamino)biphenyl]benzene. Both compounds have been characterized by single-crystal X-ray diffraction analyses. Molecule L1 forms extended two-dimensional layered structure, while L2 forms interpenetrating columnar stacks in the solid state, as revealed by X-ray diffraction analyses. Nanowire structures based on columnar stacks through self-assembly of L2 on a graphite surface were revealed by an STM study. Molecules L1 and L2 are capable of binding to metal ions, resulting in unusual structural motifs. Two Ag 1 complexes with the formulae of [(AgNO3)2(L1) (1) and [(AgNO3)3(L1) (2) were isolated from the reactions of AgNO3 with L1. Compound 1 displays extended intermolecular π-π stacking interactions that are responsible for its extended two-dimensional structure in the crystal lattice, Complex 2 has a bowl shape and forms polar stacks in the crystal lattice. A Cu II complex with the formula of [{Cu(NO3)2} 6(L2) (3) was isolated from the reaction of Cu(NO3) 2 with compound L2. The six CuII ions in 3 are chelated by the 2,2′-dipyridylamino groups of the star ligand L2. Intermolecular Cu-O (nitrate) bonds lead to the formation of an extended two-dimensional coordination network of 3. Both L1 and L2 are blue luminescent. Their interactions with AgI or CuII cause drastic quenching of emission. In addition, the luminescence of L1 and L2 is sensitive to the presence of protons, which cause a reduction of emission intensity and a red shift of the emission energy.
Hexa-substituted benzene derivatives as hole transporting materials for efficient perovskite solar cells
Liu, Yuan,Tao, Chen,Xie, Guohua,Van Der Velden, Jeroen,Marras, Sergio,Luo, Zhenghui,Zeng, Xuan,Petrozza, Annamaria,Yang, Chuluo
, p. 267 - 273 (2019)
Two low cost hexa-substituted benzene derivatives, namely HFB-OMeDPA and HPB-OMeDPA, have been successfully utilized as hole transporting materials (HTMs) for efficient perovskite solar cells (PSCs). The relationships between molecular structure, electronic properties of the semiconductor and eventually the photovoltaic performance are investigated. The planar PSCs employing HPB-OMeDPA as HTM exhibit excellent power conversion efficiencies exceeding 16% under AM 1.5G illumination conditions, which are comparable to the reference cells based on spiro-OMeTAD.
Multiexcitonic Triplet Pair Generation in Oligoacene Dendrimers as Amorphous Solid-State Miniatures
Chi, Chunyan,Hong, Yongseok,Kim, Dongho,Kim, Hyungjun,Kim, Juno,Oh, Juwon,Teo, Hao Ting
supporting information, p. 20956 - 20964 (2020/08/24)
Singlet fission in organic semiconducting materials has attracted great attention for the potential application in photovoltaic devices. Research interests have been concentrated on identifying working mechanisms of coherent SF processes in crystalline so
Undoped organic hole-transport material, preparation method and perovskite solar cell
-
Paragraph 0043; 0046; 0047, (2019/01/13)
The invention belongs to the technical field of photovoltaic materials, and particularly relates to an undoped organic hole-transport material, a preparation method and a perovskite solar cell. The material is HPB-OMe or HTB-OMe. The method comprises the
Structural complexity induced by topology change in hybrids consisting of hexa-: Peri -hexabenzocoronene and polyhedral oligomeric silsesquioxane
Zhang, Meng-Yao,Zhou, Sheng,Pan, Hong-Bing,Ping, Jing,Zhang, Wei,Fan, Xing-He,Shen, Zhihao
supporting information, p. 8679 - 8682 (2017/08/09)
Organic-inorganic hybrids with hexa-peri-hexabenzocoronene (HBC) and polyhedral oligomeric silsesquioxane (POSS) were designed and synthesized. The increase of the POSS content (or a change in topology) results in more complex self-assembled structures. This work provides a new approach for the design and synthesis of materials with sub-10 nm sizes.
Reticular Chemistry at Its Best: Directed Assembly of Hexagonal Building Units into the Awaited Metal-Organic Framework with the Intricate Polybenzene Topology, pbz-MOF
Alezi, Dalal,Spanopoulos, Ioannis,Tsangarakis, Constantinos,Shkurenko, Aleksander,Adil, Karim,Belmabkhout, Youssef,O'Keeffe, Michael,Eddaoudi, Mohamed,Trikalitis, Pantelis N.
supporting information, p. 12767 - 12770 (2016/10/13)
The ability to direct the assembly of hexagonal building units offers great prospective to construct the awaited and looked-for hypothetical polybenzene (pbz) or "cubic graphite" structure, described 70 years ago. Here, we demonstrate the successful use of reticular chemistry as an appropriate strategy for the design and deliberate construction of a zirconium-based metal-organic framework (MOF) with the intricate pbz underlying net topology. The judicious selection of the perquisite hexagonal building units, six connected organic and inorganic building blocks, allowed the formation of the pbz-MOF-1, the first example of a Zr(IV)-based MOF with pbz topology. Prominently, pbz-MOF-1 is highly porous, with associated pore size and pore volume of 13 ? and 0.99 cm3 g-1, respectively, and offers high gravimetric and volumetric methane storage capacities (0.23 g g-1 and 210.4 cm3 (STP) cm-3 at 80 bar). Notably, the pbz-MOF-1 pore system permits the attainment of one of the highest CH4 adsorbed phase density enhancements at high pressures (0.15 and 0.21 g cm-3 at 35 and 65 bar, respectively) as compared to benchmark microporous MOFs.
