20830-63-1

Basic information

• Product Name: heptacyclo[8.6.6.6~2,9~.0~3,8~.0~11,16~.0~17,22~.0~23,28~]octacosa-3,5,7,11,13,15,17,19,21,23,25,27-dodecaene-1,9-dicarbaldehyde (non-preferred name)
• CAS NO: 20830-63-1
• Molecular Formula: C₃₀H₂₀O₂
• Molecular Weight: 412.4786
• Mol File: 20830-63-1.mol

Chemical Properties

• Boiling Point: 478.1°C at 760 mmHg
• Flash Point: 177.4°C
• Density: 1.389g/cm³
• Vapor Pressure: 2.66E-09mmHg at 25°C
• Refractive Index: 1.791
• CAS DataBase Reference: heptacyclo[8.6.6.6~2,9~.0~3,8~.0~11,16~.0~17,22~.0~23,28~]octacosa-3,5,7,11,13,15,17,19,21,23,25,27-dodecaene-1,9-dicarbaldehyde (non-preferred name)(CAS DataBase Reference)
• NIST Chemistry Reference: heptacyclo[8.6.6.6~2,9~.0~3,8~.0~11,16~.0~17,22~.0~23,28~]octacosa-3,5,7,11,13,15,17,19,21,23,25,27-dodecaene-1,9-dicarbaldehyde (non-preferred name)(20830-63-1)
• EPA Substance Registry System: heptacyclo[8.6.6.6~2,9~.0~3,8~.0~11,16~.0~17,22~.0~23,28~]octacosa-3,5,7,11,13,15,17,19,21,23,25,27-dodecaene-1,9-dicarbaldehyde (non-preferred name)(20830-63-1)

Safety Data

• Hazardous Substances Data: 20830-63-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
Heptacyclo[8.6.6.6~2,9~.0~3,8~.0~11,16~.0~17,22~.0~23,28~]octacosa-3,5,7,11,13,15,17,19,21,23,25,27-dodecaene-1,9-dicarbaldehyde (non-preferred name) is used as a key intermediate in the synthesis of various organic compounds. Its complex structure and aldehyde functional groups make it a valuable building block for the development of new molecules with specific properties and applications.
Used in Materials Science:
In the field of materials science, heptacyclo[8.6.6.6~2,9~.0~3,8~.0~11,16~.0~17,22~.0~23,28~]octacosa-3,5,7,11,13,15,17,19,21,23,25,27-dodecaene-1,9-dicarbaldehyde (non-preferred name) is utilized as a component in the design and fabrication of advanced materials. Its unique arrangement of carbon atoms and aromatic rings can contribute to the development of materials with enhanced properties, such as improved stability, conductivity, or selectivity.
Used in Pharmaceutical Research:
Heptacyclo[8.6.6.6~2,9~.0~3,8~.0~11,16~.0~17,22~.0~23,28~]octacosa-3,5,7,11,13,15,17,19,21,23,25,27-dodecaene-1,9-dicarbaldehyde (non-preferred name) is employed as a potential candidate for drug discovery and development. Its complex and asymmetrical shape, along with the presence of aldehyde functional groups, may allow for the design of novel pharmaceutical agents with specific biological activities. Researchers can explore its potential as a precursor for the synthesis of new drugs or as a modulator of biological pathways.

Upstream product

• 120-12-7 anthracene 
• 642-31-9 9-anthracene aldehyde 

Downstream Products

• 642-31-9 9-anthracene aldehyde 
• 71-43-2 benzene 

Relevant articles and documents

The [4 + 4] thermocyclization of 9-anthraldehyde: synthesis, crystal structure, experimental and theoretical UV spectra, natural bonding orbital analysis and prediction of third-order nonlinear optical properties

The dimer of 9-anthraldehyde, namely heptacyclo[8.6.6.62,9.03,8.011,16.017,22.023,28]octacosa-3,5,7,11,13,15,17(22),18,20,23(28),24,26-dodecaene-1,9-carbaldehyde, C30H20O2, has been synthesized by refluxing an ethanol solution in the presence of M(ClO4)2 and 1,3-diaminopropan-2-ol (M = Co2+ or Cu2+). Its structure has been determined by single-crystal X-ray diffraction, showing it to be a new polymorph, referred to as polymorph II, in the monoclinic space group P21/n. It is compared with the previously reported triclinic modification [Ehrenberg (1968). Acta Cryst. B24, 1123–1125], which is referred to as polymorph I. The asymmetric unit of polymorph II contains two half molecules located on crystallographic centres, while the asymmetric unit of polymorph I includes one half molecule, also located on a crystallographic centre. Time-dependent density functional theory (TD-DFT) at the RB3LYP level using the 6-31G(d,p) basis set was applied. The predicted electronic absorption spectrum is in good agreement with the experimental one. The analysis of the calculated electronic absorption spectrum of polymorph II was carried out in order to assign the observed electronic transitions and to determine their character. A natural bonding orbital (NBO) analysis was executed at the same level to evaluate charge-transfer, intramolecular hydrogen-bonding interactions and hyperconjugative interactions. The third-order nonlinear optical (NLO) properties of the compound were appraised by the ZINDO/sum-over-states method in both static and dynamic states. The orientationally averaged (isotropic) value of γ for the compound is greater than the corresponding value of 4-nitroaniline (pNA).

Fluorescence sensing of microcracks based on cycloreversion of a dimeric anthracene moiety

Novel fluorescent crack sensors have been developed based on dimeric anthracene moiety-containing polymers. Two anthracene derivatives, 9-anthraldehyde (AA) and 9-anthracenecarboxylic acid (AC), were photodimerized to obtain cyclooctane-type dimers. Crack-sensing polymers (Poly-AA and Poly-AC) were prepared by crosslinking of poly(vinyl alcohol) by using the dimers as crosslinkers. The polymers afforded transparent, hard coatings. Upon cracking, the polymers exhibited strong optical absorption and fluorescence emission while the uncracked original polymers did not. This was explained by regeneration of the anthracene moiety by mechanochemical cycloreversion of the cyclooctane dimer structure. It was found that the crack planes emitted fluorescence having emission maxima in the range of 500-600 nm when excited with 330-385 nm UV light. Absolute fluorescence quantum yield measurements indicated that the polymers could have good capability of fluorescence crack sensing. Preliminary evaluation of the crack-sensing ability of Poly-AA and Poly-AC was performed with the polymer films, and fluorescence emission was clearly observed along the crack planes upon excitation with 330-385 nm UV light. Poly-AA and Poly-AC are promising as fluorescent crack sensors because the anthracene moiety regenerated upon cracking has relatively long excitation and emission wavelengths as well as strong fluorescence. The Royal Society of Chemistry 2012.

High conversion and selectivity of photodimerization under air conditions by supramolecular oxidation restraint within a metallocage-like nanoreactor

The well-designed metal-organic cage Ce-BHP, with a size-suitable cavity, functional interaction sites and a flexible backbone, could encapsulate 9-anthraldehyde molecules and act as a nanoreactor via supramolecular behavior, avoiding the undesired oxidation forming 9,10-anthraquinone, and also as an efficient catalyst to successfully achieve high conversion of single photodimers under air conditions. This journal is