Difference between revisions of "Highly polycyclic small molecule"

Revision as of 18:20, 18 May 2022

This page is about small molecules that feature a lot of polycyclic elements.
Polycycles not just in in 2D but also (and perhaps predominately so) in 3D.
Preferably with no free rotational degrees of freedom in the molecule.

Such molecules may eventual provide a way out of the
fat finger problem vs floppy finger problem dilemma
that one faces with natural proteins.

Highly polycyclic small molecule could be integrated as an artificial side-chain in synthetic peptides.
For integration of different technologies see page:
Combining advantages of different selfassembly technologies

Examples

Spiroligomers

These are:

• typically 2D polycyclic
• do not allow for any rotational degrees of freedom

See main page: Spiroligomers

Adamantane related building blocks

This is about molecules close to adamantane in structure.
These are close in nature to diamond. And the origin of the name diamondoid.

One proposal is the synthesis and usage of adamantanes with corners substituted with boron and/or nitrogen.

• Either alternatingly wit 4 nitrogen atoms and 4 boron atoms
• Or two different molecules.
  One with all 8 substituted with nitrogen (adamanzane aka 1,3,5,7-tetraazaadamantane).
  The other one with all 8 substituted with boron (??? aka 1,3,5,7-tetraboroadamantane).

The idea is (wiki-TODO: verify that) that unlike open carbon bonds (carbon radicals)
the unreacted boron and nitrogen could be stable in some solvents.

Formed B-N coordinative bonds between the buildingblocks would be only slightly weaker than C-C bonds.
As can be seen in the super-hard artificial gemstone boron nitride (today only ceramics).

There are actually quite many strong covalent bond forming reactions that can happen between in-solvent-stable molecules.
After all these reactions are the basis for a lot of modern chemistry.
For an overview over such reactions see page: Types of chemical reactions for synthesis

Optically active molecules

Many of these own their optical activity form delocalized electrons in graphitic polycycles within the molecule.
Some of these even do conformational changes on optical activation.
So these could, beside their stiffness provide the functionality of optically activated nanoscale actuators.

Misc

Aromatic polycyclic compounds are also often optically active
and potentially of interest as basis for optically activated nanoscale actuators.

Related

• The "downward inward" aspect of: Expanding the kinematic loop
• Stiffness
• Combining advantages of different selfassembly technologies
• Spiroligomers
• Organometallic compound
• Molecule fragments

• Types of chemical reactions for synthesis

External links

Adamantane related work

Awesome graphics thereto (and coupling to nanotubes) on www.somewhereville.com
In peculiar this slide: Dative-Based Molecular Building Blocks – Graphic by Damian G. Allis – Idea by Ralph C. Merkle (2000)

• 2020 Complexes Between Adamantane Analogues B4X6 -X = {CH2, NH, O ; SiH2, PH, S} - and Dihydrogen, B4X6:nH2 (n = 1–4)
  at www.mdpi.com
• 2018 Adamantane-Derived Carbon Nanothreads: High Structural Stability and Mechanical Strength
  at pubs.acs.org
• 2009 Functionalized adamantane: Building blocks for nanostructure self-assembly
  at journals.aps.org
• 2008 Electronic nature of the aromatic adamantanediyl ions and its analogues
  at www.scielo.br

Wikipedia

• Adamanzane – adamantane with corners substituted by nitrogen atoms
• The boron analogon to adamanzane
• The alternating nitrogen boron version of adamanzane

• Adamantane
• Diamondoid
• Staffane
• Category: Adamantanes
• Category: Adamantane like molecules

• Category: Polycyclic organic compounds
• Category: Polycyclic onaromatic hydrocarbons
• Category: Boron heterocycles
• Heterocyclic compound
• Category: Heterocyclic compounds
• Category: Nitrogen heterocycles

• Category: Cluster chemistry

Exotic miscellaneous:

• Azaborane
• Carboranes