208-69-5

Usage

Alias

Tetracyclopentacene

Chemical Structure

Consists of five fused benzene rings

Conjugation

Highly conjugated molecule

Applications

Organic Electronics: Studied for potential use in OLEDs and OPVs
Material Science: Unique electronic and optical properties make it promising for various technologies

Synthetic Precursor

Explored for synthesis of complex organic compounds due to its unique structure and reactivity

Health and Environmental Impacts

Carcinogenic and Mutagenic Properties: Potential risks due to its polycyclic aromatic hydrocarbon nature
Environmental Pollution: May be present as a pollutant in certain settings

Upstream product

• 42081-22-1 spiro 
• 83469-44-7 1-anthracene 
• 70909-33-0 1-(methoxymethyl)anthracene 
• 252-16-4 1H-cyclobutaanthracene 
• 235426-11-6 9-anthracene 

Relevant academic research and scientific papers

C15H10 and C15H12 Thermal Chemistry: Phenanthrylcarbene Isomers and Phenylindenes by Falling Solid Flash Vacuum Pyrolysis of Tetrazoles

2-Phenyl-5-(phenylethynyl)tetrazole 44 provides a new entry to the C15H10 energy surface. Flash vacuum pyrolysis of 44 using the falling solid flash vacuum pyrolysis (FS-FVP) method afforded cyclopenta[def]phenanthrene 31 and cyclope

Preparative methodology and pyrolytic behavior of anthrylmonocarbenes: Synthesis and chemistry of 1H-cyclobuta[de]anthracene

This study involves (1) the behavior of organolithium reagents (1-6), (2) development of efficient methods for preparing 9(7)- and 1(8)- [methoxy(trimethylsilyl)methyl]anthracenes and their analogues, (3) the intramolecular chemistry of the 9(9)- and 1(10)-anthrylcarbenes generated by pyrolyses of 7 and 8, respectively, and (4) investigation of thermal behavior and bromination of the 1H-cyclobuta[de]anthracene (11) obtained from 9 or 10. α-Methoxy-9-anthrylmethyllithium (1), prepared from 9- (methoxymethyl)anthracene (14) and t-BuLi in TMEDA/Et2O/pentane, reacts at C-10 with D2O, chlorotrimethylsilane, dimethyl sulfate, benzoyl chloride, acetaldehyde, benzaldehyde, and acetone to give, after neutralization, 9,10- dihydro-9-(methoxymethylene)-10-substituted-anthracenes 15 and 21a-f. However, lithiation of 9-(thiomethoxymethyl)anthracene (25) with t- BuLi/TMEDA/Et2O/pentane occurs by an apparent radical-anion displacement process to give 9-anthrylmethyllithium (3), which then reacts with chlorotrimethylsilane to yield 9-(trimethylsilylmethyl)anthracene (28). Similarly, 28 is formed from 25 and from 9- (trimethylsilyloxymethyl)anthracene (29) with lithium and then chlorotrimethylsilane. The electrophiles D2O, dimethyl sulfate, and benzaldehyde react with 3 at its methyl and its C-10 positions. [Methoxy(trimethylsilyl)methyl]arenes 40-42 and 7 are obtained by reactions of their aryllithium and arylmagnesium bromide precursors with bromo(methoxy)methyltrimethylsilane (39). 1-(Methoxymethyl)anthracene (45) is converted conveniently by t-BuLi and chlorotrimethylsilane to 8. Flash- vacuum pyrolyses of 7 and 8 yield 11 preparatively; 11 then thermolyzes to 2H-cyclopenta[jk]fluorene (46). Decomposition of 9-deuterio-10- [methoxy(trimethylsilyl)methyl]anthracene (55) at 650 °C/10-3 mm results in 10(56)- and 1(57)-deuteriocyclobutanthracenes, thus revealing that the 10- deuterio-9-anthrylcarbene inserts to give 56 and also isomerizes extensively before yielding 57. Of note is that 56 isomerizes thermally by C10-D movement to form 2-deuteriocyclopentafluorene 58, 57 rearranges by C10-H movement to yield deuteriocyclopentafluorene 59, and 58 and 59 equilibrate 1,5-sigmatropically. Possible mechanisms for the isomerizations of 56 and 57 are outlined. Further, bromine adds rapidly to 11 to form 9,10-dibromo-9,10- dihydro-1H-cyclobuta[de]anthracene (94), which eliminates HBr on warming to yield 10-bromo-1H-cyclobuta[de]anthracene (95).