194-32-1

Basic information

• Product Name: cyclohepta[fg]acenaphthylene
• Synonyms: Acepleiadylene; cyclohept[fg]acenaphthylene; Cyclohepta[fg]acenaphthylene
• CAS NO: 194-32-1
• Molecular Formula: C₁₆H₁₀
• Molecular Weight: 202.2506
• Mol File: 194-32-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 653.7°C at 760 mmHg
• Flash Point: 286.8°C
• Density: 1.24g/cm³
• Vapor Pressure: 3.04E-16mmHg at 25°C
• Refractive Index: 1.742
• CAS DataBase Reference: cyclohepta[fg]acenaphthylene(CAS DataBase Reference)
• NIST Chemistry Reference: cyclohepta[fg]acenaphthylene(194-32-1)
• EPA Substance Registry System: cyclohepta[fg]acenaphthylene(194-32-1)

Safety Data

• Hazardous Substances Data: 194-32-1(Hazardous Substances Data)

Upstream product

• 518-03-6 acepleiadiene 
• 108-67-8 1,3,5-trimethyl-benzene 
• 518-02-5 1,2,5,6,7,8-hexahydrocyclohepta[fg]acenaphthylene 
• 19190-91-1 5,6-dibromoacenaphthene 

Downstream Products

• 518-03-6 acepleiadiene 
• 518-02-5 1,2,5,6,7,8-hexahydrocyclohepta[fg]acenaphthylene 

Relevant articles and documents

Revisiting Acepleiadylene: Two-Step Synthesis and π-Extension toward Nonbenzenoid Nanographene

Acepleiadylene (APD), a nonbenzenoid nonalternant isomer of pyrene, exhibits different electronic properties from pyrene, but has been rarely studied since its first synthesis in 1956, probably due to the difficulties in synthesis and further derivatization. In this work, we revisited this long-known compound and developed a new two-step synthetic route to efficiently access APD on the gram scale. Theoretical and experimental characterizations elucidated the unique properties of APD as compared with its benzenoid isomer pyrene, particularly revealing its dipolar structure with a narrow optical gap. The functionalization of APD was demonstrated for the first time, providing doubly brominated APD as a key precursor for further π-extension. As a proof of concept, a π-extended APD and a cyclotrimer nanographene (C48H24) were constructed, opening up new avenues to nonbenzenoid nanographenes with low HOMO-LUMO gaps.

Synthesis method and derivation method of non-benzene type polycyclic aromatic hydrocarbon APD and derivative of non-benzene type polycyclic aromatic hydrocarbon APD

The invention discloses a synthesis method of non-benzene type polycyclic aromatic hydrocarbon APD , which comprises: (1) a coupling reaction: carrying out a reaction on 5, 6-disubstituted acenaphthene or acenaphthene, a C4 synthon, a transition metal catalyst, a ligand and an alkali in a solvent to obtain a compound B; and (2) dehydrogenation reaction: heating the compound B and an oxidizing agent in a solvent for reaction to obtain a product. According to the method, APD is efficiently synthesized through a two-step method, the total yield reaches up to 44% or above, gram-level synthesis of APD can be achieved, and a foundation is laid for further research and derivatization of APD. The invention also provides a derivation method of APD, a bromine-containing key compound is synthesized through bromination of APD, a foundation is laid for subsequent derivation reactions such as coupling and ring closing, and a series of diversified substituted APD derivatives with novel structures are synthesized through derivatization design. A series of organic conjugated molecules which are diversified in structure and take APD as cores are synthesized through pi expansion.

Structure and Reactivity of Polycyclic Ion Pairs

A series of polycyclic ?-systems 1-5 which have in common a naphthalene moiety are reduced by alkali metals: via the intermediate radical anions the corresponding dianion salts and a tetraanion salt of 1 are obtained.The structures of the ion pairs are elucidated by spectroscopic methods.The charge distribution depends on the topology of the ?-systems and on the polarizing counterions.Knowledge of the charge distribution allows to rationalize the reactions of the dianions with electrophiles.