55805-81-7

Usage

Uses

Used in Laboratory Research and Development:
2,3,6,7,12,13-hexabromotriptycene is used as an impurity standard and reference substance for various laboratory research and development processes. Its unique chemical structure and properties make it a valuable tool for studying chemical reactions and understanding the behavior of similar compounds.
Used in Chemical Production Processes:
In the chemical production industry, 2,3,6,7,12,13-hexabromotriptycene serves as an important intermediate or additive in the synthesis of various compounds. Its presence can help improve the efficiency and yield of certain chemical reactions, contributing to the overall production process.

Synthesis

Triptycene (1.06 g, 4.18 mmol) was dissolved in chloroform (80 mL) in a round-bottom flask. Iron filings (30 mg) were added, and the solution was stirred at 25 °C. Bromine (1.35 mL, 26.3 mmol) was added, and the solution was refluxed for 1 h, during which time the initially reddish-brown solution turned reddish-orange. The flask was removed from heat, and chloroform and excess bromine were removed under vacuum. The resulting brown powder was dissolved in chloroform (100 mL) and flushed through a pad of silica using additional chloroform as eluent (100 mL). The filtrate was evaporated to dryness. The crude white powder (2.83 g, 98%) was crystallized from acetone yielding C20H8Br6 · (acetone)2 (0.88 g, 29%), mp >350 °C. The mother liquor was evaporated and the residue was crystallized from acetone to afford a second crop of crystals (0.97 g, C20H8Br6 · (acetone)2, 32%). The combined yield was 1.85 g, 61%: 2-H yield 2.83 g, 98%

Upstream product

• 477-75-8 triptycene 

Downstream Products

• 1835723-12-0 2,3,6,7,14,15-hexa(4′-formylphenyl)triptycene 
• 1227256-04-3 2,3,6,7,12,13-hexahydroxytriptycene 

Relevant academic research and scientific papers

A Robust 3D Cage-like Ultramicroporous Network Structure with High Gas-Uptake Capacity

A three-dimensional (3D) cage-like organic network (3D-CON) structure synthesized by the straightforward condensation of building blocks designed with gas adsorption properties is presented. The 3D-CON can be prepared using an easy but powerful route, whi

A triphenylene-based triptycene with large free volume synthesized by zirconium-mediated biphenylation

(Chemical Equation Presented) Biphenylation using (Li(THF) 4)2·Zr(biphe)3 of hexabromotriptycenes bearing H (1-H) or Bu (1-Bu) at the bridgeheads gave triptycenes with triphenylene blades. The blades extend both perpendicu

High CO2 uptake and selectivity by triptycene-derived benzimidazole-linked polymers

Successful incorporation of triptycene into benzimidazole-linked polymers leads to the highest CO2 uptake (5.12 mmol g-1, 273 K and 1 bar) by porous organic polymers and results in high CO2/N 2 (63) and CO2

Three-dimensional triptycene-based covalent organic frameworks with ceq or acs topology

The growth of three-dimensional covalent organic frameworks (3D COFs) with new topologies is still considered as a great challenge due to limited availability of high-connectivity building units. Here we report the design and synthesis of 3D triptycene-ba

Three-Dimensional Triptycene-Functionalized Covalent Organic Frameworks with hea Net for Hydrogen Adsorption

Owing to the finite building blocks and difficulty in structural identification, it remains a tremendous challenge to elaborately design and synthesize three-dimensional covalent organic frameworks (3D COFs) with predetermined topologies. Herein, we report the first two cases of 3D COFs with the non-interpenetrated hea net, termed JUC-596 and JUC-597, by using the combination of tetrahedral and triangular prism building units. Due to the presence of triptycene functional groups and fluorine atoms, JUC-596 exhibits an exceptional performance in the H2 adsorption up to 305 cm3 g?1 (or 2.72 wt%) at 77 K and 1 bar, which is higher than previous benchmarks from porous organic materials reported so far. Furthermore, the strong interaction between H2 and COF materials is verified through the DFT theoretical calculations. This work represents a captivating example of rational design of functional COFs based on a reticular chemistry guide and demonstrates its promising application in clean energy storage.

Linear acene compound based on triptycene and synthesis and application thereof

The invention discloses a linear acene compound based on triptycene and synthesis and application thereof. The structural formula of the compound is shown as T-X, wherein in the structural formula, the substituted position is 2-position or 3-position; if yes, the benzene ring is of a benzoquinone structure; i is a natural number of 0-5; R is a substituted or non-substituted silyl ethynyl group, asubstituted or non-substituted alkyl ethynyl group, a substituted or non-substituted alkoxy ethynyl group, a substituted or non-substituted aryl ethynyl group, a substituted or non-substituted heterocyclic aryl ethynyl group, a substituted or non-substituted heterocyclic ethynyl group, a substituted or non-substituted silane group, a substituted or non-substituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic aryl group, a substituted or unsubstituted heterocyclic group or a hydrogen atom; and when R is a hydrogen atom, i is not 0. According to the invention, the triptycene is used as a parent nucleus for the first time to design and synthesize the trimer of the linear acene compound, and theapplication of the triptycene in organic photoelectric devices is researched.

Towards molecular construction platforms: Synthesis of a metallotricyclic spirane based on bis(2,2′:6′,2"-terpyridine)RuII connectivity

The design and construction of the first multicomponent stepwise assembly of a II-tpy>-based (tpy=terpyridine), three-dimensional, propeller-shaped trismacrocycle, 8, are reported. Key steps in the synthesis involve the preparation of a

Triptycene-based polymers of intrinsic microporosity: Organic materials that can be tailored for gas adsorption

We report the synthesis and properties of network polymers of intrinsic microporosity (network - PIMs) derived from triptycene monomers that possess alkyl groups attached to their bridgehead positions. Gas adsorption can be controlled by the length and branching of the alkyl chains so that the apparent BET surface area of the materials can be tuned within the range 618 - 1760 m2 g- 1. Shorter (e.g., methyl) or branched (e.g., isopropyl) alkyl chains provide the materials of greatest microporosity, whereas longer alkyl chains appear to block the microporosity created by the rigid organic framework. The enhanced microporosity, in comparison to other PIMs, originates from the macromolecular shape of the framework, as dictated by the triptycene units, which helps to reduce intermolecular contact between the extended planar struts of the rigid framework and thus reduces the efficiency of packing within the solid. The hydrogen adsorption capacities of the triptycene-based PIMs with either methyl or isopropyl substituents are among the highest for purely organic materials at low or moderate presures (1.83% by mass at 1 bar/77K; 3.4% by mass at 18 bar/77 K). The impressive hydrogen adsorption capacity of these materials is related to a high concentration of subnanometre micropores, as verified by Horvath - Kawazoe analysis of low-pressure nitrogen adsorption data.