Triptycene (1) is a three-bladed molecule synthesized by P. D. Bartlett et al. in 1942. The structure of 1 is rigid, 120° orienting, and three-pronged, so it was named after "the triptych of antiquity".1,2)
1 has been investigated as a part of molecular machines because of its unique structure. For example, a molecular bevel gear which has a cyclopropenium ring with three triptycenes is synthesized by using of 9-bromotriptycene (2).3)
Furthermore, it has been reported that the synthesis of the 9-triptycylselenol kinetically stabilized by a sterically-crowded triptycene component, followed by the reaction of 9-triptycylselenol with a palladium complex resulted in the production of the five-membered selenapalladacycle.4,5)
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A Molecule like Three-bladed Gear
References
- 1)Triptycene (9,10-o-benzenoanthracene)
- 2)Triptycene derivatives: synthesis and applications
- 3)Stereochemical consequences of a parity restriction on dynamic gearing in tris(9-triptycyl)germanium chloride and tris(9-triptycyl)cyclopropenium perchlorate
- 4)Preparation of a selenenic acid and isolation of selenoseleninates
- 5)Reactions of 9-triptyceneselenol with palladium(0) complexes: unexpected formations of the dinuclear palladium(I) complex [{Pd(PPh3)}2(μ-SeTrip)2] and five-membered selenapalladacycle [Pd(η2(C,Se)-Trip)(dppe)]
