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Conjugation The Key to Color of Organic Molecules & Dyestuffs

Why Most of the Organic Molecules Don't Show Any Color?


Organic molecules absorb light in the UV region.
From the basics of color theory, we know that we perceive an object in a color lets say yellow
because it absorbs the complementary color of yellow (which is violet) & reflects it.
Now, our visible spectrum of color ranges from 400 nm 700 nm (in wavelength). So in order
to see a color the object must absorb the wavelength of light in between this range. Organic
molecules doesn't do so.

Fig: Diagram Showing Different Rays with Their Wavelengths

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Conjugation The Key to Color of Organic Molecules & Dyestuffs

Fig: Complementary Colors

Organic molecules generally absorb the wavelength of light in the UV region which is
below 400 nm. As a result they dont show any color.

How Can We Introduce Color in Organic Molecules? / Why Dyestuffs Show Color?

If we want to give the answer in one word we would say Conjugation.

What is Conjugation?
A molecule is conjugated if the pi electrons in the p orbitals can be shared by 3 or more than
3 atoms. It is possible by the alternating single & double bond. This allows a delocalization of
pi electrons across all the adjacent aligned p-orbitals. The pi electrons do not belong to a single
bond or atom, but rather to a group of atoms. One of the simplest conjugated molecules is 1,3butadiene.

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Conjugation The Key to Color of Organic Molecules & Dyestuffs

Fig: 1,3-butadiene & its conjugated system containing 4 Atomic Orbitals

Anyway, what we need to remember here is that conjugated molecules are lower in energy &
stable.

The energy difference between the HOMO (Highest Occupied Molecular Orbital) &
LUMO (Lowest Un-occupied Molecular Orbital) is less.
By conjugating an organic molecule we can introduce color.

Basic Concept:
We know that Energy of light corresponds to a wavelength. When it is directed at a molecule,
the electrons from the Bonding Molecular Orbital will jump on to the Anti-bonding Molecular
Orbital temporarily & thus it absorbs some energy which tells us what wavelength of light will
be absorbed by the molecule. If the wavelength of light absorbed falls in the visible spectrum
region (400 nm 700 nm) than well see a color.

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Conjugation The Key to Color of Organic Molecules & Dyestuffs

Mechanism:

From this equation we can see that Energy is inversely proportional to wavelength.

So, the lower the Energy gap between HOMO & LUMO the higher the wavelength of
light absorbed.

Now lets calculate wavelength from energy for some molecules:


Ethylene Molecule:

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Conjugation The Key to Color of Organic Molecules & Dyestuffs

It contains two p orbital hence two Atomic Orbital & according to MO theory the two atomic
orbital will form two Molecular Orbital. One is Bonding & Other one is Anti-bonding. The Energy
difference between these two orbitals is 173 kcal/mol. So, by putting this value in equation (1)
we get the wavelength which is 165 nm & it falls in the UV range.
1,3 Butadiene:

Here, 4 Pi Atomic Orbital = 4 Pi Molecular Orbital. 2 is bonding & other 2 is anti-bonding. The
Energy difference between these two orbitals is 132 kcal/mol. The wavelength corresponding
to this value is 217 nm which is also in the UV range.
1,3,5-Hexatriene:

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Conjugation The Key to Color of Organic Molecules & Dyestuffs

Here, 6 Pi Atomic Orbital = 6 Pi Molecular Orbital. 6 is bonding & other 6 is anti-bonding.The


Energy difference between these two orbitals is 111 kcal/mol. The wavelength corresponding
to this value is 258 nm which is also in the UV range.

So, let's compare these 3 molecules -

What we can observe from here is that, the more conjugation/delocalization/joining-up there
is, the smaller the energy gap between the HOMO and LUMO. So wavelength increases.
Now lets see an organic molecule which shows color:
Beta Carotene:

Fig: Beta Carotene

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Conjugation The Key to Color of Organic Molecules & Dyestuffs

As we can see, the beta carotene molecule which is found in carrots have 11 conjugated
carbon as a result the energy gap is very low. This molecule absorbs the wavelength of light
around 455 nm. So, it absorbs blue color & reflects its complementary color which
is Orange (See the figure of complementary colors above).

Application:

Acid-Base Indicators like Phenolphthalein, Methyl orange etc. (Here, Conjugation


increases & decreases corresponding to pH).

Synthesis of dyes like Mauve, Indigo etc.

Bleaching process (Here the bleach only destroys the conjugation of stain/dirt so we
cant see any dirt but its still there)
Its practiced mostly in Dye companies.

Watch this video for further clarification.

References
[1] James. (2014, 10 01). Are these molecules conjugated? Retrieved from Master Organic Chemistry:
http://www.masterorganicchemistry.com/2011/03/08/are-these-alkenes-conjugated/
[2] Ultraviolet and visible spectroscopy. (2014, 10 01). Retrieved from ChemWiki:
http://chemwiki.ucdavis.edu/Organic_Chemistry/Organic_Chemistry_With_a_Biological_Empha
sis/Chapter_04%3A_Structure_Determination_I/Section_4.3%3A_Ultraviolet_and_visible_spect
roscopy
[3] UV-Visible Absorption Spectra. (2014, 10 01). Retrieved from chemguide:
http://www.chemguide.co.uk/analysis/uvvisible/theory.html

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