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US 2020/0010419 A1Published application
Nanohoop compound embodiments comprising meta-substitution and molecular systems comprising the same
AssigneeUniversity of Oregon
InventorsRamesh Jasti, Jeff Van Raden
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Abstract
Disclosed herein are embodiments of nanohoop compounds, methods of making, and methods of using the same. The nanohoop compounds disclosed herein have discrete ring system(s) that comprise a unique meta-substituted motif that affords a strained cavity in which myriad reaction chemistries can take place. The unique structures and properties of the nanohoop compounds disclosed herein also lend to their use in a variety of biological applications, and as interlocked structures in molecular machines.
Claims20
A nanohoop compound, having a structure satisfying Formula 1
- wherein
- each RS ring independently has a structure satisfying Formula II
- wherein at least one X is N, P, or C-CFG, wherein CFG is a coordinating functional group;
- each other X independently is C or C(R1) where R1 is selected from an electron-accepting group or an electron-donating group;
- and r and t independently are 0 or 1;
- each A and A′ ring independently is an aromatic ring;
- each R independently is selected from hydrogen, an electron-donating group, an electron-accepting group, or any combinations thereof;
- m is an integer selected from 1 to 4;
- m′ is an integer selected from 0 to 4;
- each s and s′ independently is an integer selected from 0 to 4;
- each n and n′ independently is an integer selected from 0 to 24;
- and
- p is an integer selected from 1 to 20.
10 more elements
A method of making a nanohoop compound, comprising:
- cross-coupling a compound having a structure satisfying a Formula A with a RS precursor having a structure satisfying a Formula B to provide a substituted nanohoop precursor having a structure satisfying a compound C;
- and
- deprotecting the substituted nanohoop precursor to provide the substituted nanohoop compound;
- wherein
- Formula A is
- Formula B is
- and
- Formula C is
- and wherein each PG independently is a silyl protecting group, each LG independently is a leaving group selected from chloro, fluoro, bromo, or iodo, each s and s′ can independently be an integer selected from 0 to 4;
- and each n and n′ can independently be an integer selected from 0 to 24.
7 more elements
Dependencies are inferred from the claim text.