196316-30-0

Upstream product

• 1633-22-3 [2.2]Paracyclophan 
• 553-94-6 4-bromo-m-xylene 
• 4519-36-2 (4-methylbenzyl)-trimethylammonium chloride 
• 1633-22-3 [2.2]paracyclophane 
• 23927-40-4 S_p-pseudo-ortho-dibromo[2.2]paracyclophane 
• 23927-40-4 (Rp)‐4,12‐dibromo[2.2]paracyclophane 

Downstream Products

• 344938-52-9 4,12-dimethyl<2.2>paracyclophane 
• 162103-24-4 4,16-bis(4-methoxyphenyl)-<2.2>paracyclophane 
• 162103-23-3 4,16-bis(2,4,6-trimethylphenyl)-<2.2>paracyclophane 
• 24262-20-2 1,4(1,4)-dibenzenacyclohexaphane-1²,4³-diol 
• 23927-40-4 (Rp)‐4,12‐dibromo[2.2]paracyclophane 
• 670274-27-8 4,12-bis[4'-(methylthio)styryl][2.2]paracyclophane 
• 1062306-89-1 rac-4-bromo[2.2]paracyclophan-13-ylenediphenylphosphine 
• 364732-88-7 4,12-bis(diphenylphosphino)-[2.2]-paracyclophane 
• 95274-32-1 pseudo-o-dibenzoyl<2.2>paracyclophane 
• 107496-61-7 [1-[14-(Hydrazono-phenyl-methyl)-tricyclo[8.2.2.2^4,7]hexadeca-1⁽¹³⁾,4⁽¹⁶⁾,5,7⁽¹⁵⁾,10⁽¹⁴⁾,11-hexaen-5-yl]-1-phenyl-meth-(Z)-ylidene]-hydrazine 
• 1186137-46-1 4-benzhydrylideneamino-12-bromo[2.2]paracyclophane 
• 1353683-39-2 C₅₀H₅₄BrNO₂S 
• 1353683-40-5 C₃₉H₃₁NOS 
• 1353683-41-6 C₄₃H₃₃NOS₂ 

Relevant academic research and scientific papers

Improved synthesis of (±)-4,12-dihydroxy[2.2]paracyclophane and Its enantiomeric resolution by enzymatic methods: Planar chiral (R)- and (S)-phanol

(±)-4,12-Dihydroxy[2.2]paracyclophane [(±)-PHANOL] is readily prepared from [2.2]paracyclophane by an improved synthetic protocol. Enzymatic kinetic resolution of its bis-acetate proceeds with good enantioselection. Separation, hydrolysis, and recrystallization provides both enantiomers of PHANOL in high enantiopurity.

Influencing the Self-Sorting Behavior of [2.2]Paracyclophane-Based Ligands by Introducing Isostructural Binding Motifs

Two isostructural ligands with either nitrile (Lnit) or isonitrile (Liso) moieties directly connected to a [2.2]paracyclophane backbone with pseudo-meta substitution pattern have been synthesized. The ligand itself (Lnit) or its precursors (Liso) were resolved by HPLC on a chiral stationary phase and the absolute configuration of the isolated enantiomers was assigned by XRD analysis and/or by comparison of quantum-chemical simulated and experimental electronic circular dichroism (ECD) spectra. Surprisingly, the resulting metallosupramolecular aggregates formed in solution upon coordination of [(dppp)Pd(OTf)2] differ in their composition: whereas Lnit forms dinuclear complexes, Liso exclusively forms trinuclear ones. Furthermore, they also differ in their chiral self-sorting behavior as (rac)-Liso undergoes exclusive social self-sorting leading to a heterochiral assembly, whereas (rac)-Liso shows a twofold preference for the formation of homochiral complexes in a narcissistic self-sorting manner as proven by ESI mass spectrometry and NMR spectroscopy. Interestingly, upon crystallization, these discrete aggregates undergo structural transformation to coordination polymers, as evidenced by single-crystal X-ray diffraction.

Chiroptical properties of oligophenylenes anchoring with stereogenic [2.2]paracyclophane

To elucidate the effect of π-conjugation length on chiroptical properties in circular dichroism (CD) and circularly polarized luminescence (CPL) spectra, stereogenic oligophenylenes containing biphenyl and terphenyl units linked by a planar chiral [2.2]paracyclophane were synthesized. Both compounds are highly emissive, and their chiroptical responses depend on the conjugation length. However, extended π-conjugation exhibited smaller dissymmetry factor (g-value) both in absorption and emission spectra.

Cyclophanes. Part LII: Ethynyl[2.2]paracyclophanes - New building blocks for molecular scaffolding

The synthesis of seven ethynyl[2.2]paracyclophanes is described. The five diethynyl derivatives 4,5-diethynyl[2.2]paracyclophane (12), pseudo-gem-(13), pseudo-ortho-(14), pseudo-meta-(15), and pseudo-para-diethynyl[2.2] paracyclophane (16), the tetraethynyl compound 4,7,13,16-tetraethynyl[2.2] paracyclophane (17), and for comparison the mono-ethynylated hydrocarbon 4-ethynyl[2.2]paracyclophane (11) have been prepared. The structures of these new building blocks for carbon rich systems were determined by the usual analytical and spectroscopic methods.

Synthesis of novel alternating π-conjugated copolymers having [2.2]paracyclophane and fluorene units in the main chain leading to the blue light-emitting materials

Novel through-space π-conjugated polymers having [2.2]paracyclophane and fluorene units were synthesized by Heck-Sonogashira coupling reaction. The polymers exhibited strong blue fluorescence in solution and in the solid state.

A two-year water-stable 2D MOF with aqueous NIR photothermal conversion ability

Structural lability in humid air or water severely limits the practical use of MOFs. Developing new MOFs with exceptional water stability is interesting for both industrial applications and academic research. Herein we report a new method to improve the water stability of MOFs by using three-dimensional rigid shielding ligands. A very highly stable two-dimensional MOF (CuCP-MOF) is synthesized in this work, in which [2,2]paracyclophane dicarboxylate ligands are coordinated with Cu(ii) ions to form a paddle wheel structure. CuCP-MOF is a triclinic crystal with unit cell parametersa= 10.065 ?,b= 10.897 ?,c= 10.940 ?,α= 90.676°,β= 91.729°, andγ= 92.725° determined by single crystal X-ray diffraction and DFT simulation. It can easily form MOF nanosheets due to the large interlayer distance and weak interlayer interactions. It shows good aqueous stability, and remains intact after storage in water for two years, as evidenced by FTIR and XRD analyses. CuCP-MOF shows a strong absorption in the NIR range due to the d-d transition of Cu(ii). The aqueous dispersions of CuCP-MOF exhibit high NIR photothermal conversion efficiency, about 17.5% for a laser with an energy density of 5 W cm?2(808 nm) and 22.0% for a laser of 2 W cm?2on average.

Soluble polybenzimidazoles with intrinsic porosity: Synthesis, structure, properties and processability

We have explored two novel comonomers, namely, 4,16-dicarboxyl[2.2]paracyclophane and 5,5′,6,6′-tetraamino-3,3,3′,3′-tetramethyl-1,1′-spirobi[indane], for the synthesis of co-polybenzimidazoles (co-PBIs) with intrinsic porosity. Both these monomers possess twisted structures that can lead to “awkward” macromolecular shapes that cannot pack efficiently. The consequences of introducing these two monomers on the structure and properties of PBIs are reported. The random copolymers synthesized are amorphous and possess glass transition temperatures (Tgs) greater than 400?°C. Tg decreases with increasing comonomer content indicating an increase in fractional free volume. The copolymers have low surface area. TEM and BET measurements show evidence of mesopore formation. The copolymers show significant carbon dioxide adsorption. Single chain molecular dynamics simulation of 24-mer repeat units shows intramolecular void spaces arising as a result of distorted polymer chain with reduced conformational mobility. These studies define a new synthetic strategy for “bottoms-up” synthesis of PBIs with intrinsic porosity.

Synthesis and chiroptical properties of stereogenic cyclic dimers based on 2,2′-biselenophene and [2.2]paracyclophane

Stereogenic cyclic dimers based on 2,2′-biselenophene linked with [2.2]paracyclophane have been synthesized to investigate their chiroptical properties. Embedding selenophene led to the formation of intramolecular Se?π interactions between the two biselenophene strands. The resulting rigid cyclic system exhibits enhanced chiroptical properties when compared with its precursor. In addition, the electrochemical properties were also investigated.

Through-space π-delocalization in a conjugated macrocycle consisting of [2.2]paracyclophane

Herein, we report the synthesis and characterization of a [2.2]paracyclophane-containing macrocycle (PCMC) as a new through-space conjugated macrocycle using only benzene groups as the skeleton. For comparison, a diphenylmethane-containing nanohoop macrocycle (DCMC) with a non-conjugated linker was also synthesized. Their structures were confirmed by NMR and HR-MS, and their photophysical properties were studied by UV-vis and fluorescence spectroscopies combined with theoretical calculations. The strain energy of PCMC was estimated to be as high as 72.58 kcal mol-1.

Regioselective Synthesis of 4,7,12,15-Tetrasubstituted [2.2]Paracyclophanes: A Modular Route Involving Optical Resolution

A practical synthetic method for preparing bis-(para)-pseudo-ortho and bis-(para)-pseudo-meta type 4,7,12,15-tetrasubstituted [2.2]paracyclophanes is reported. Regioselective double Rieche formylation was successfully applied to the corresponding dibromo[2.2]paracyclophanes under slightly modified conditions. Aldehydes reacted in an unknown direction with Rieche formylation agents, dichloromethyl methyl ether and titanium(IV) tetrachloride, leading to the formation of benzal chlorides. Formylated products were obtained after hydrolysis of these benzal chloride derivatives. Optical resolution was performed with the diastereomer method and (RP)-4,12-dibromo-7,15-diformyl[2.2]paracyclophane was successfully obtained in an enantiomerically pure form (99 % ee). Their synthetic utility is demonstrated with some exploratory transformations to access corresponding differently functionalized tetrasubstituted [2.2]paracyclophane derivatives.