36288-15-0

Upstream product

• 36288-05-8 C₂₀H₂₀ 
• 63409-06-3 7-methyl-1-naphthalenecarboxaldehyde 
• 221102-56-3 αα-(6-methylindane)-β-(p-toluyl) propanoic acid 
• 221102-62-1 6-methyl-1-(2-p-tolyl-ethyl)-indan-1-carboxylic acid ethyl ester 
• 221102-67-6 C₂₀H₂₀O 
• 221102-72-3 6,7'-dimethyl-3',4'-dihydrospiro-1'-ol 
• 139300-29-1 3,9-Dimethyl-1,2,3,4-tetrahydro-chrysene 

Relevant academic research and scientific papers

Infinitene: A Helically Twisted Figure-Eight [12]Circulene Topoisomer

New forms of molecular nanocarbon particularly looped polyarenes adopting various topologies contribute to the fundamental science and practical applications. Here we report the synthesis of an infinity-shaped polyarene, infinitene (1) (cyclo[c.c.c.c.c.c.e.e.e.e.e.e]dodecakisbenzene), comprising consecutively fused 12-benzene rings forming an enclosed loop with a strain energy of 60.2 kcal·mol–1. Infinitene (1) represents a topoisomer of still-hypothetical [12]circulene, and its scaffold can be formally visualized as the outcome of the “stitching” of two homochiral [6]helicene subunits by both their ends. The synthetic strategy encompasses transformation of a rationally designed dithiacyclophane to cyclophadiene through the Stevens rearrangement and pyrolysis of the corresponding S,S′-bis(oxide) followed by the photocyclization. The structure of 1 is a unique hybrid of helicene and circulene with a molecular formula of C48H24, which can be regarded as an isomer for kekulene, [6,6]carbon nanobelt ([6,6]CNB), and [12]cyclacene. Infinitene (1) is a bench-stable yellow solid with green fluorescence and soluble to common organic solvents. Its figure-eight molecular structure was unambiguously confirmed by X-ray crystallography. The scaffold of 1 is significantly compressed as manifested by a remarkably shortened distance (3.152–3.192 ?) between the centroids of two π–π stacked central benzene rings and the closest C···C distance of 2.920 ?. Fundamental photophysical properties of 1 were thoroughly elucidated by UV–vis absorption and fluorescence spectroscopic studies and density functional theory calculations. Its configurational stability enabled separation of the corresponding enantiomers (P,P) and (M,M) by a chiral HPLC. Circular dichroism (CD) and circularly polarized luminescence (CPL) measurements revealed that 1 has moderate |gCD| and |gCPL| values.

Synthesis of substituted 3′, 4′-dihyrospiro [indane-1, 2′(1′H) naphthalene]-1′-ols and their catalytic dehydrogenation

Catalytic dehydrogenation of 5′, 7′-dimethyl-3′, 4′-dihydrospiro[indane-1, 2′(1′H) naphthalene]-1′-ol 5a, 7′-ethyl-3′,4′-dihydrospiro[indane-1, 2′-(1′H) naphthalene]-1′-ol 5b, 6-methyl-3′, 4′-dihydrospiro[indane-1, 2′(1′H) naphthalene]-1′-ol 5c and 6, 7′-dimethyl-3′, 4′-dihydrospiro[indane-1, 2′(1′H) naphthalene]-1′-ol 5d affords 1, 3-dimethylchrysene 6a, a mixture of 3-ethyl chrysene 6b and chrysene, 3-methylchrysene 6c and 3, 9-dimethylchrysene 6d, respectively. Condensation of anhydride of 1a of 1-carboxyindane-1-acetic acid with m-xylene and ethylbenzene give ketoacids 2a and 2b while 2c and 2d are obtained by condensation of the anhydride 1b of 1-carboxy-6-methylindane-1-acetic acid with benzene and toluene respectively. Catalytic reduction in acetic acid solution of 2a, 2c, 2d, and in ethanolic solution of 2b, give 3a, 3c, 3d and 3b. In ethanolic solution, 2c and 2d give esters 3cE and 3dE. Intramolecular acylation of 3a, 3b, 3c and 3cE and 3d and 3dE give 4a, 4b, 4c and 4d which after LAH reduction followed by dehydrogenation gave chrysenes 6a, 6b, 6c and 6d. Structures of all compounds corroborate their spectral data.

Synthesis of substituted chrysenes

3,9-Dimethylchrysene (8) and 3,9,11-trimethylchrysene (8a) have been synthesised involving the following steps: 2-(7'-methyl-1'-naphthyl)ethyl bromide (5) and 2-(7'-methyl-1'-naphthyl)propyl bromide (5a) are condensed separately with 2-carbethoxy-5-methylcyclohexanone to afford ethyl α,α-(5-methyl-1-ketocyclohexane)-γ-(7'-methyl-1'-naphthyl)butanoate (6) and ethyl α,α-(5-methyl-1-ketocyclohexane)-γ-(7'-methyl-1'-naphthyl)pentanoate (6a) respectively.PPA cyclisation of 6 and 6a followed by aromatisation afford 8 and 8a.