Synthesis and properties of 1,6,7,12,13,18,19,24-octamethylacenaphthyleno[b,l]tetraphenylene

Abstract

The X-ray crystal structure and photophysical properties of 1,6,7,12,13,18,19,24-octamethylacenaphthyleno[b,l]tetraphenylene, which has been synthesized via a Diels-Alder reaction of 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctene and 6,7-dihydro-6-hydroxy-7,9-dimethyl-8H-cyclopenta[a]acenaphthylene-8-one, are reported.

Strained Dehydrobenzoannulenes

“…[40] [4+2] Cycloaddition of 14a with a cyclopentadienone derivative possessing a fluoranthene unit gave 30 which may be transformed into a corranulene-tetraphenylene hybrid. [41] Wudl utilized reactive diene 31 in a [4+2] cycloaddition reaction with 14a to give a new diene 32 through the subsequent thermal extrusion of phenyl isocyanate. [42] A second cycle of the same sequence of reactions, that is, with 14a and 32, furnished the tetrabenzo-fused [2.2.…”

Our Expedition in Eight‐Membered Ring Compounds: From Planar Dehydrocyclooctenes to Tub‐Shaped Chiral Tetraphenylenes

“…The synthesis was accomplished via Diels-Alder reaction between the cyclopentadienone 109 and 18 (Scheme 17). [38] The X-ray crystal structure reveals a C2 symmetric molecule with a severely twisted surface. The twisting is continuous from one naphthalene subunit, through the tetraphenylene core, to the naphthalene of the other fluoranthene subunit.…”

“…Siegel reported the synthesis and properties of a novel saddle‐shaped tetraphenylene derivative 110 containing two fluoranthene subunits. The synthesis was accomplished via Diels–Alder reaction between the cyclopentadienone 109 and 18 (Scheme ) . The X‐ray crystal structure reveals a C 2 symmetric molecule with a severely twisted surface.…”

Synthesis of tetraphenylene derivatives and their recent advances

“…The research group of Siegel reported a novel saddle-shaped tetraphenylene derivative (44) containing two fluoranthene subunits [36]. The synthesis was achieved via a Diels-Alder reaction between 43 and 19 (Scheme 13).…”