5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isophthalaldehyde

CAS Number 945865-80-5

Chemistry Building Blocks, COF Ligands, Materials, Porous Organic Frameworks

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isophthalaldehyde MSDS

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isophthalaldehyde CAS 945865-80-5

Covalent organic frameworks (COFs) isophthalaldehyde ligand

a versatile ligand used for synthesising COFs and macromolecules with applications in iodine capture, OLEDs and light induced hydrogen generation

Overview
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5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isophthalaldehyde (CAS number 945865-80-5) is an isophthalaldehyde that contains a pinacolborate group (tetramethyl dioxaboranyl, Bpin). With two aldehyde groups, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isophthalaldehyde can crosslink with amines for producing COFs with imine linkages. The Bpin group allows for its combination with other functional molecules such as pyrenes through the Suzuki-Miyaura cross-coupling reaction. The resulting pyrene-isophthalaldehyde reacts with cyclohexanediamine forming a COF cage, which is studied for its photocatalytic reaction of converting benzeneboronic acid to phenol with a 99% conversion. The functionalities of the COFs cages are versatile and dependent on the specific functional molecules employed in the reaction. For instance, the inclusion of bipyridine provides the COFs cage with the ability to capture iodine (up to 5.8 g/g).

Benzimidazole-triazine based materials for exciplex-OLEDs can be prepared from 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isophthalaldehyde, triazine derivatives and N-phenyl-o-phenylenediamine. The exciplex-OLEDs exhibit luminous efficacy of 80.4 lm/W, current efficiency of 60.1 cd/A and external quantum efficiency of 18.4%.

Duo functionality

Enabling post-functionalisation

High Purity

>98% Purity

Worldwide shipping

Quick and reliable shipping

MOF and COF ligands

Aldehyde and Bpin ligand for cross-linked COF networks

General Information

CAS Number	945865-80-5
Chemical Formula	C₁₄H₁₇BO₄
Full Name	5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isophthalaldehyde
Molecular Weight	260.09 g/mol
Synonyms	5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,3-dicarbaldehyde
Classification / Family	Isophthalaldehydes, Dioxaborolanes, COFs, Macromolecules, Iodine capture, OLEDs, Hydrogen evolution, Photocatalysts

Chemical Structure

Product Details

Purity	98%
Melting Point	N/A
Appearance	White to off-White powder

MSDS Documentation

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isophthalaldehyde MSDS Sheet

Literature and Reviews

Tuning molecular chromophores of isoreticular covalent organic frameworks for visible light-induced hydrogen generation, W. Li et al., Adv. Funct. Mater., 32, 2207394(2022); DOI: 10.1002/adfm.202207394.
Stimuli-responsive porous molecular crystal with reversible modulation of porosity, N. Sun et al., ACS Appl. Mater. Interfaces, 14(1), 1519–1525(2021); DOI: 10.1021/acsami.1c18368.
Benzimidazole-triazine based exciplex films as emitters and hosts to construct highly efficient OLEDs with small efficiency roll-off, B. Liang et al., J. Mater. Chem. C, 8, 2700–2708(2020); DOI: 10.1039/C9TC06212B.
Transformation of porous organic cages and covalent organic frameworks with efficient iodine vapor capture performance, C. Liu et al., J. Am. Chem. Soc., 144(27), 12390–12399(2022); DOI: 10.1021/jacs.2c03959.
Porous pyrene organic cage with unusual absorption bathochromic-shift enables visible light photocatalysis, N. Sun et al., CCS Chem., 4, 2588–2596(2022); DOI: 10.31635/ccschem.021.202101202.

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