1

Non-planar aromatic
compounds
 Requirements of the problem 2

• Explain the existence of non-planar aromatic

compounds.
• Describe the influence of non-planarity on physico-
chemical properties of aromatic compounds.
• Describe possible approaches for creating such
molecules.
 Non-planar aromatic compounds 3
existence
• The incorporation of a non-
six-membered rings into the
aromatic skeleton

• The incorporation of an
appropriate bridge or
bridges

• Through non-bonded
interactions
 Pyrenphanes
4

Pyrene
it is the smallest peri-fused
1polycyclic aromatic
hydrocarbon
[2.2]paracyclophane
The cyclophanes consist of an
aromatic system in which two
nonadjacent atoms on this system are
connected by a bridge, which can be
any series of atoms.

Pyrenophanes
Molecule
By VID method
The pyrenophane parent 5

The molecule that I

analyzed was
1:2,13:14-
Dibenzo[2]paracyclo[2](2,7)pyreno
phane-1,13-diene
Measurement of the angle
The angles were calculated through DFT-calculations 6
C1
C8
The bent
angle C2
C3 C6
C7

The non-planarity of any pyrene can

be quantified by the bend angle,
which is the smallest angle between
the C1-C2-C3 and C6-C7-C8 planes.
 How the bent angle affect the
aromaticity 7
There are 13 unique pairs of (1,3), (1,4), (1,5),
nonadjacent carbon atoms in pyrene (1,6), (1,7), (1,8),
that could serve a bridgeheads in a (1,9), (2,4), (2,5),
cylcophane (2,6), (2,7), (4,9)
The more strained the
molecule is, the more easily The more highly strained a
the molecule can lose it pyrenophane becomes, the more
aromaticity due to suffer some reactive the pyrene system within it
reaction where double bound becomes
would be affected

The shorter the bridged bounds are, the

angle will decrease so the molecule
would be fine strained
Properties of the non-planar aromatic
8
molecule HOMA and NICS indicate 92−98%
retention of aromaticity of the highly
Aromaticity retention distorted pyrene systems compared to
planar pyrene.

fluorescent probes have been

Creation of electroluminescent designed that take advantage of
devices . excimer/monomer emission and
long fluorescence lifetime

It possibly works while the process

Plastics, dye , pesticides
in different process in these
pharmaceutical
industries