Delocalization
leads to a lowering of energy levels and narrowing of the spacings
between levels; and the larger the delocalized system, the greater
this effect. This can be seen in the series of aromatic molecules
compared at the bottom of the opposite page. Benzene has six atoms
in its delocalized p- electron system,
and the spacings between the p-orbital
energy levels are such that it absorbs energy at a set of wavelengths
in the ultraviolet region, centered around 2550 Å. The visible
wavelengths pass through the molecule untouched, so benzene is colorless
to our eyes. So are naphthalene and anthracene, which have 10 and
14 atoms in the delocalized system, although the larger rings shift
the absorption to longer wavelengths or lower energies: 3150 Å
and 3800 Å. In contrast, delocalization in naphthacene is
so extensive that the splitting between ir energy levels has narrowed
to the point where blue light around 4800 Å is absorbed. With
the blue light absorbed, the remaining visible wavelengths make
naphthacene appear orange, the complement of blue. In pentacene,
which has five rings, absorption is shifted down to even lower energies.
Pentacene removes yellow light around 5800 Å and therefore
appears indigo. This "eyeball spectroscopy" is surprisingly informative
in revealing what aromatic molecules are doing. The visible spectrum
is shown at the right, with colors recorded as a function of wavelength
from the ultraviolet to the infrared. If any of these wavelengths
is absorbed by a molecule, the remaining wavelengths give the molecule
the complementary color. Removal of green wavelengths around 5300
Å makes a molecule appear purple. If the molecule absorbs
red light at around 6800 Å, we will see it as blue-green.
By looking at what is left of the visible spectrum after absorption,
we can decide approximately what visible wavelengths the compound
is absorbing.