76197-35-8

Usage

Uses

Used in Organic Synthesis:
2,3-Anthracenedicarboxaldehyde is used as a key intermediate in the synthesis of various organic compounds. Its aldehyde functional groups allow for a wide range of chemical reactions, making it a valuable building block in the production of pharmaceuticals, dyes, and other specialty chemicals.
Used in Materials Science:
In the field of materials science, 2,3-Anthracenedicarboxaldehyde is utilized for its potential applications in the development of new materials with unique properties. Its electronic and optical characteristics make it a promising candidate for use in the creation of advanced materials with applications in areas such as electronics, photonics, and energy storage.
Used in Photophysics and Photochemistry:
2,3-Anthracenedicarboxaldehyde is employed as a reagent in photophysical and photochemical studies due to its ability to absorb and emit light. This property allows researchers to investigate its behavior under various conditions, leading to a better understanding of its potential applications in light-driven processes and reactions.
Used as a Fluorescent Probe:
In biological and environmental research, 2,3-Anthracenedicarboxaldehyde serves as a fluorescent probe for detecting and measuring the presence of certain molecules. Its fluorescence properties enable the visualization and quantification of target molecules, making it a valuable tool in analytical chemistry and bioimaging.
Used in Sensing and Imaging Technologies:
2,3-Anthracenedicarboxaldehyde has been investigated for its potential use in the development of new technologies for sensing and imaging applications. Its unique properties make it a candidate for the creation of sensors with high sensitivity and selectivity, as well as imaging agents that can provide detailed information about the molecular environment.

InChI:InChI=1/C16H10O2/c17-9-15-7-13-5-11-3-1-2-4-12(11)6-14(13)8-16(15)10-18/h1-10H

Upstream product

• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 643-79-8 o-phthalic dicarboxaldehyde 
• 7149-49-7 2,3-naphthalenedicarboxaldehyde 
• 1134642-63-9 (3-hydroxymethyl-anthracen-2-yl)-methanol 
• 31554-15-1 2,3-bis(hydroxymethyl)naphthalene 

Relevant academic research and scientific papers

Isoacenofuran: A novel quinoidal building block for efficient access to high-ordered polyacene derivatives

Herein, a simple and practical method for generating isoacenofuran, a new π-extended quinoidal building block, was developed. A three-step protocol involving double nucleophilic additions of alkynyllithiums to acene-2,3-dicarbaldehyde, mono-oxidation, and acid-promoted cyclization enables the generation of the target molecule, which is trapped by a dienophile to produce highly condensed acenequinones. Further transformations by double nucleophilic additions of alkynyllithium to hexacenequinone, followed by reductive aromatization, produce tetraalkynylhexacenes with a remarkably higher stability than that of the previously reported substituted hexacenes.

Phosphine-Mediated Iterative Arene Homologation Using Allenes

A PPh3-mediated multicomponent reaction between o-phthalaldehydes, nucleophiles, and monosubstituted allenes furnishes functionalized non-C2-symmetric naphthalenes in synthetically useful yields. When the o-phthalaldehydes were reacted with 1,3-disubstituted allenes in the presence of PPh2Et, naphthalene derivatives were also obtained in up to quantitative yields. The mechanism of the latter transformation is straightforward: aldol addition followed by Wittig olefination and dehydration. The mechanism of the former is a tandem γ-umpolung/aldol/Wittig/dehydration process, as established by preparation of putative reaction intermediates and mass spectrometric analysis. This transformation can be applied iteratively to prepare anthracenes and tetracenes using carboxylic acids as pronucleophiles.

Iterative synthesis of acenes via homo-elongation

Starting from aromatic ortho-dialdehydes, we devised a homo-elongation protocol that combines a Wittig olefination and subsequent intramolecular Knoevenagel condensation to produce acene diesters and dinitriles. The Royal Society of Chemistry.

First-order hyperpolarizability of oligo-acene derivatives by hyper-Rayleigh scattering

First-order hyperpolarizabilities β for a series of oligo-acene derivatives were estimated as a function of the conjugation length by means of the hyper-Rayleigh scattering (HRS) technique. Satisfactory data acquisition and analyses gave the hyperpolarizabilities (17 ± 2) × 10-30 and (68 ± 8) × 10-30 esu for naphthalene-2,3-dialdehyde and anthracene-2,3-dialdehyde, respectively. The pure β value of tetracene-2,3-dialdehyde (OA4) could not be determined because of multiphoton absorption induced fluorescence superimposed on the HRS signal. A large β value (≈ 180 × 10-30 esu) is expected for OA4 by extrapolating the conjugation length dependence on β.