935-50-2Relevant articles and documents
Concave-Convex π-π Template Approach Enables the Synthesis of [10]Cycloparaphenylene-Fullerene [2]Rotaxanes
Xu, Youzhi,Kaur, Ramandeep,Wang, Bingzhe,Minameyer, Martin B.,Gs?nger, Sebastian,Meyer, Bernd,Drewello, Thomas,Guldi, Dirk M.,Von Delius, Max
, p. 13413 - 13420 (2018)
The cycloparaphenylenes (CPPs) are a class of strained macrocycles that until 2008 were considered beyond the reach of organic synthesis. With its cyclic array of ten para-substituted phenylene rings, [10]CPP possesses a concave π-system that is perfectly preorganized for the strong supramolecular association of convex fullerenes such as C60. Although mechanically interlocked CPP architectures have been observed in the gas phase, the rational synthesis of bulk quantities has not been achieved yet, which is likely due to the fact that conventional template strategies are not amenable to CPP rings that lack heteroatoms. Here, we report the synthesis of two [2]rotaxanes in which a [10]CPP ring binds to a central fullerene bis-adduct and is prevented from dethreading by the presence of two bulky fullerene hexakis-adduct stoppers. The final step in the rotaxane synthesis is surprisingly efficient (up to ca. 40% yield) and regioselective because the fullerene acts as an efficient convex template, while [10]CPP acts as a supramolecular directing group, steering the reaction at the central fullerene exclusively toward two trans regioisomers. Comprehensive physicochemical studies confirmed the interlocked structure, shed light on the dynamic nature of the CPP-fullerene interaction, and revealed intriguing consequences of the mechanical bond on charge transfer processes. In light of recent advances in the synthesis of nanohoops and nanobelts, our concave-convex π-π templating strategy may be broadly useful and enable applications in molecular electronics or complex molecular machinery.
1,3-Diradicals Embedded in Curved Paraphenylene Units: Singlet versus Triplet State and In-Plane Aromaticity
Miyazawa, Yuki,Wang, Zhe,Matsumoto, Misaki,Hatano, Sayaka,Antol, Ivana,Kayahara, Eiichi,Yamago, Shigeru,Abe, Manabu
supporting information, p. 7426 - 7439 (2021/05/29)
Curved π-conjugated molecules and open-shell structures have attracted much attention from the perspective of fundamental chemistry, as well as materials science. In this study, the chemistry of 1,3-diradicals (DRs) embedded in curved cycloparaphenylene (
METHOD FOR PRODUCING ANNULAR COMPOUND
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Paragraph 0149-0152, (2020/11/25)
PROBLEM TO BE SOLVED: To provide a method for producing an annular compound which can be produced in high yield. SOLUTION: There is provided a method for producing an annular compound represented by formula (M) comprising reacting particular two kinds of reactive compounds in the presence of a transition metal complex and an organic base. [In Formula (M), m' represents an integer of 5 to 15, and n' represents an integer of 1 to 10. Ara represents a group in which hydrogen atoms have been removed one by one from two sp3 carbons included in an arylene group or the like. However, at least one of Ara represents a group in which hydrogen atoms have been removed one by one from two sp3 carbons included in a cycloalkadiene, and these groups may have a substituent. Arb represents a group in which hydrogen atoms have been removed one by one from two sp3 carbons included in an arylene group or the like, and these groups may have a substituent.] SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
