Synthesis, aromatization and cavitates of an oxanorbornene-fused dibenzo[de,qr]tetracene nanobox

Abstract

Oxanorbornene-fused double-stranded macrocycles, as represented by kohnkene, are not only synthetic precursors toward short segments of zigzag carbon nanotubes but also typical cavitands processing an intrinsic cavity. However, their capability...

An oxanorbornene-fused nanocage consisting of hexaazatrinaphthylene and pyrene units

“…It is worth noting that detection of the fully conjugated target molecules only by HRMS is in fact not rare in the reported challenging syntheses of highly curved molecular nanocarbons, such as carbon nanobelts. 15,36–38…”

“…It is worth noting that detection of the fully conjugated target molecules only by HRMS is in fact not rare in the reported challenging syntheses of highly curved molecular nanocarbons, such as carbon nanobelts. 15,[36][37][38] Nanocage 1 has a unique structure consisting of two π-electron deficient hexaazatrinaphthylene (HATN) units and three π-electron rich pyrene units, which are connected through sp 3 bridgehead carbon atoms. This situation is similar to that in the triptycene-based donor-acceptor systems, where the π-donor and π-acceptor interact through homoconjugation.…”

“…Owing to the curved and rigid nature of oxanorbornene, oxanorbornene-fused building blocks have been demonstrated to be very useful in synthesizing a series of double-stranded macrocycles, which are precursors of zigzag carbon nanobelts in the reported syntheses with complete 9,10 or partial success. [11][12][13][14][15] On the other hand, oxanorbornene-fused building blocks have been rarely used in constructing organic nanocages, except trinacrene, which was synthesized by Stoddart and coworkers in 1989. 16,17 Nanocage 1 is closely related to trinacrene but differs from it by containing N atoms in its polycyclic framework.…”

Functionalized Hydrocarbon Belts: Synthesis, Structure and Properties

“…[12][13][14][15] The subsequent aromatization reactions lead to the formation of beltarenes or cyclacenes. [9,[13][14][15] These breakthroughs have initiated a resurgence of the research area. [1-4-16] One of the noteworthy endeavors is the exploration of belt structures which contain other carbocyclic [17][18][19][20] and heterocyclic rings [21][22][23][24][25][26][27][28][29][30][31] in addition to hexagonal benzene rings.…”

Gram-scale synthesis of a covalent nanocage that preserves the redox properties of encapsulated fullerenes

“…, porphyrins, 2 d , f ,4 a ,10 naphthalene or perylene diimides, 8 a ,11 pyrenes, 12 anthracenes, 13 etc. 14 ) often show particularly high affinities for binding fullerenes due to the large π–π overlap provided upon complexation. However, the synthesis of such hosts is typically challenging or costly, either relying on the stoichiometric use of precious metals to link the aromatic walls‡‡For fullerene receptors utilizing precious metals as linking agents for aromatic walls, see ref.…”