quinoxaline-2,3-dicarboxylic acid

• CAS: 6924-99-8
• Catalog Number: ACM6924998
• Category: Main Products
• Molecular Weight: 218.17
• Molecular Formula: C10H6N2O4
• Synonyms: 2,3-Dicarboxyquinoxaline
• Appearance: Solid

Case Study

Quinoxaline-2,3-Dicarboxylic Acid as a Gateway to Dipolar Unsymmetrical Benzoporphyrins

Galanin, N. E., et al. Russian Journal of Organic Chemistry 43.7 (2007): 1080-1086.

Porphyrin-based macrocycles with large intrinsic dipole moments are of significant interest for nonlinear optics and molecular electronics. This work employed quinoxaline-2,3-dicarboxylic acid-derived intermediates to synthesize unsymmetrical tetrabenzoporphyrins featuring electron-withdrawing quinoxaline and electron-donating tert-butylbenzene moieties within a single macrocycle. The resulting cis-di(4-tert-butylbenzo)diquinoxalinoporphyrin exhibits pronounced molecular polarization.
Experimental Protocol: Quinoxaline-2,3-dicarboxylic acid was converted to its corresponding dicarboximide by passing dry ammonia through the molten acid at 250 degrees C. A stepwise condensation strategy was employed: 4-tert-butylphthalimide was first dimerized with zinc acetate to produce a bis-isoindole intermediate, which subsequently reacted with the quinoxaline-2,3-dicarboximide and malonic acid in the presence of zinc acetate at elevated temperatures (260-330 degrees C). The zinc complexes were isolated by column chromatography on alumina, then demetallated using concentrated sulfuric acid to yield the free-base porphyrins. Characterization included electronic absorption, ¹H NMR, IR spectroscopy, and AM1 semiempirical calculations.
Performance Evaluation: The zinc complex of the unsymmetrical diquinoxalinoporphyrin displayed a Soret band at 429 nm and Q-bands at 584 and 631 nm in chloroform, with a weak charge-transfer absorption at 492 nm. In the metal-free form, the Soret band was split and red-shifted by 45-47 nm relative to unsubstituted tetrabenzoporphyrin, indicative of strong molecular polarization. AM1 calculations confirmed a significantly non-planar macrocycle for the diquinoxaline derivative. The pronounced dipole character and extended conjugation make these compounds promising candidates for optoelectronic applications.

Custom Q&A

What is the molecular formula of quinoxaline-2,3-dicarboxylic acid?

The molecular formula of quinoxaline-2,3-dicarboxylic acid is C10H6N2O4.

What is another name for quinoxaline-2,3-dicarboxylic acid?

Another name for quinoxaline-2,3-dicarboxylic acid is 2,3-quinoxalinedicarboxylic acid.

What is the CAS number of quinoxaline-2,3-dicarboxylic acid?

The CAS number of quinoxaline-2,3-dicarboxylic acid is 6924-99-8.

What is the IUPAC name of quinoxaline-2,3-dicarboxylic acid?

The IUPAC name of quinoxaline-2,3-dicarboxylic acid is quinoxaline-2,3-dicarboxylic acid.

What is the InChIKey of quinoxaline-2,3-dicarboxylic acid?

The InChIKey of quinoxaline-2,3-dicarboxylic acid is CQZDWYYGOZOTHY-UHFFFAOYSA-N.

What is the molecular weight of quinoxaline-2,3-dicarboxylic acid?

The molecular weight of quinoxaline-2,3-dicarboxylic acid is 218.17 g/mol.

How many hydrogen bond donor counts are present in quinoxaline-2,3-dicarboxylic acid?

There are 2 hydrogen bond donor counts present in quinoxaline-2,3-dicarboxylic acid.

How many hydrogen bond acceptor counts are present in quinoxaline-2,3-dicarboxylic acid?

There are 6 hydrogen bond acceptor counts present in quinoxaline-2,3-dicarboxylic acid.

What is the topological polar surface area of quinoxaline-2,3-dicarboxylic acid?

The topological polar surface area of quinoxaline-2,3-dicarboxylic acid is 100Ų.

Is quinoxaline-2,3-dicarboxylic acid a covalently-bonded unit?

Yes, quinoxaline-2,3-dicarboxylic acid is a covalently-bonded unit.