Crystal Structures of 5,6,5′,6′-Tetramethoxy-1,1′-spirobisindane-3,3′-dione and two of its Fluorene Adducts

Carta, Mariolino; Raftery, James; McKeown, Neil B.

doi:10.1007/s10870-010-9844-1

Cited by 8 publications

(1 citation statement)

References 15 publications

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“…Figure shows single-crystal structures of 4 , 5c , 7 , and 9b obtained by X-ray crystallographic analysis. For the purpose of comparison, we also show the crystal data of TTSBI [PIM-1 monomer (Figure b)] and O-LSBI (PIM-C1 monomer) obtained from previous publications. , As noted, the most significant change between TTSBI and O-LSBI is the angle between the two phenyl rings . As shown in Figure , O-LSBI formed a 58.5° angle between two phenyl rings, which is significantly smaller than that of the typical spirobisindane TTSBI (85.0°). , The angle in S-locked 4 is 60.6°, similar to that in O-LSBI , suggesting their similar ability with an increase in the rigidity of the archetypal TTSBI .…”

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confidence: 99%

Locking the Spiro Carbon in Spirobisindane Using Sulfur and Phosphorus to Form “Olympic Ring”-like Molecules

2022

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To improve the rigidity of spirobisindane, it was intramolecularly locked by forming eight-membered rings via sulfur and phosphorus atoms to produce an interlocked polycyclic structure under mild conditions in good yields. By carefully analyzing the crystal structures, we noticed that the angle between the two benzene rings in the locked version is significantly smaller than that of the typical spirobisindane structure. Molecular modeling indicated that locking the spiro center can remarkably enhance the rigidity.

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