A chromophore is the part of a

molecule A molecule is a group of two or more atoms that are held together by Force, attractive forces known as chemical bonds; depending on context, the term may or may not include ions that satisfy this criterion. In quantum physics, organic chemi ...

responsible for its

color Color (or colour in English in the Commonwealth of Nations, Commonwealth English; American and British English spelling differences#-our, -or, see spelling differences) is the visual perception based on the electromagnetic spectrum. Though co ...

. The word is derived . The color that is seen by our eyes is that of the light not absorbed by the reflecting object within a certain

wavelength In physics and mathematics, wavelength or spatial period of a wave or periodic function is the distance over which the wave's shape repeats. In other words, it is the distance between consecutive corresponding points of the same ''phase (waves ...

spectrum of visible light. The chromophore is a region in the molecule where the energy difference between two separate molecular orbitals falls within the range of the visible spectrum (or in informal contexts, the spectrum under scrutiny). Visible light that hits the chromophore can thus be absorbed by exciting an

electron The electron (, or in nuclear reactions) is a subatomic particle with a negative one elementary charge, elementary electric charge. It is a fundamental particle that comprises the ordinary matter that makes up the universe, along with up qua ...

from its ground state into an

excited state In quantum mechanics Quantum mechanics is the fundamental physical Scientific theory, theory that describes the behavior of matter and of light; its unusual characteristics typically occur at and below the scale of atoms. Reprinted, Add ...

. In biological molecules that serve to capture or detect light energy, the chromophore is the moiety that causes a

conformational change In biochemistry, a conformational change is a change in the shape of a macromolecule, often induced by environmental factors. A macromolecule is usually flexible and dynamic. Its shape can change in response to changes in its environment or othe ...

in the molecule when hit by light. Why_are_plants_green

Conjugated pi-bond system chromophores

Just like how two adjacent p-orbitals in a molecule will form a pi-bond, three or more adjacent p-orbitals in a molecule can form a conjugated pi-system. In a conjugated pi-system, electrons are able to capture certain photons as the electrons resonate along a certain distance of p-orbitals - similar to how a radio antenna detects photons along its length. Typically, the more conjugated (longer) the pi-system is, the longer the wavelength of photon can be captured. In other words, with every added adjacent double bond we see in a molecule diagram, we can predict the system will be progressively more likely to appear yellow to our eyes as it is less likely to absorb yellow light and more likely to absorb red light. ("Conjugated systems of fewer than eight conjugated double bonds absorb only in the ultraviolet region and are colorless to the human eye", "Compounds that are blue or green typically do not rely on conjugated double bonds alone.") In the conjugated chromophores, the electrons jump between energy levels that are extended pi orbitals, created by electron clouds like those in

aromatic In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated system, conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugati ...

systems. Common examples include

retinal Retinal (also known as retinaldehyde) is a polyene chromophore. Retinal, bound to proteins called opsins, is the chemical basis of visual phototransduction, the light-detection stage of visual perception (vision). Some microorganisms use ret ...

(used in the eye to detect light), various

food coloring Food coloring, color additive or colorant is any dye, pigment, or substance that imparts color when it is added to food or beverages. Colorants can be supplied as liquids, powders, gels, or pastes. Food coloring is commonly used in commercia ...

s, fabric dyes (

azo compound Azo compounds are organic compounds bearing the functional group diazenyl (, in which R and R′ can be either aryl or alkyl groups). IUPAC defines azo compounds as: "Derivatives of diazene (diimide), , wherein both hydrogens are substituted ...

s),

pH indicator A pH indicator is a halochromism, halochromic chemical compound added in small amounts to a Solution (chemistry), solution so the pH (acidity or Base (chemistry), basicity) of the solution can be determined visually or spectroscopically by chang ...

lycopene Lycopene is an organic compound classified as a tetraterpene and a carotene. Lycopene (from the Neo-Latin '' Lycopersicon'', the name of a former tomato genus) is a bright red carotenoid hydrocarbon found in tomatoes and other red fruits and ve ...

, β-carotene, and anthocyanins. Various factors in a chromophore's structure go into determining at what wavelength region in a spectrum the chromophore will absorb. Lengthening or extending a

conjugated system In physical organic chemistry, a conjugated system is a system of connected p-orbitals with delocalized electrons in a molecule, which in general lowers the overall energy of the molecule and increases Chemical stability, stability. It is Reson ...

with more unsaturated (multiple) bonds in a molecule will tend to shift absorption to longer wavelengths. Woodward–Fieser rules can be used to approximate

ultraviolet Ultraviolet radiation, also known as simply UV, is electromagnetic radiation of wavelengths of 10–400 nanometers, shorter than that of visible light, but longer than X-rays. UV radiation is present in sunlight and constitutes about 10% of ...

-visible maximum absorption wavelength in organic compounds with conjugated pi-bond systems. Some of these are metal complex chromophores, which contain a metal in a

coordination complex A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of chemical bond, bound molecules or ions, that are in turn known as ' ...

with ligands. Examples are

chlorophyll Chlorophyll is any of several related green pigments found in cyanobacteria and in the chloroplasts of algae and plants. Its name is derived from the Greek words (, "pale green") and (, "leaf"). Chlorophyll allows plants to absorb energy ...

, which is used by plants for photosynthesis and

hemoglobin Hemoglobin (haemoglobin, Hb or Hgb) is a protein containing iron that facilitates the transportation of oxygen in red blood cells. Almost all vertebrates contain hemoglobin, with the sole exception of the fish family Channichthyidae. Hemoglobin ...

, the oxygen transporter in the blood of vertebrate animals. In these two examples, a metal is complexed at the center of a tetrapyrrole macrocycle ring: the metal being iron in the heme group (iron in a porphyrin ring) of hemoglobin, or magnesium complexed in a

chlorin In organic chemistry, chlorins are tetrapyrrole pigments that are partially hydrogenation, hydrogenated porphyrins. The parent chlorin is an unstable compound which undergoes air oxidation to porphine. The name chlorin derives from chlorophyll. ...

-type ring in the case of chlorophyll. The highly conjugated pi-bonding system of the macrocycle ring absorbs visible light. The nature of the central metal can also influence the absorption spectrum of the metal-macrocycle complex or properties such as excited state lifetime. The tetrapyrrole moiety in organic compounds which is not macrocyclic but still has a conjugated pi-bond system still acts as a chromophore. Examples of such compounds include

bilirubin Bilirubin (BR) (adopted from German, originally bili—bile—plus ruber—red—from Latin) is a red-orange compound that occurs in the normcomponent of the straw-yellow color in urine. Another breakdown product, stercobilin, causes the brown ...

and urobilin, which exhibit a yellow color.

Auxochrome

An auxochrome is a functional group of atoms attached to the chromophore which modifies the ability of the chromophore to absorb light, altering the wavelength or intensity of the absorption.

Halochromism

Halochromism occurs when a substance changes color as the pH changes. This is a property of

s, whose

molecular structure Molecular geometry is the three-dimensional arrangement of the atoms that constitute a molecule. It includes the general shape of the molecule as well as bond lengths, bond angles, torsional angles and any other geometrical parameters that det ...

changes upon certain changes in the surrounding pH. This change in structure affects a chromophore in the pH indicator molecule. For example, phenolphthalein is a pH indicator whose structure changes as pH changes as shown in the following table: In a pH range of about 0-8, the molecule has three aromatic rings all bonded to a tetrahedral sp³ hybridized carbon atom in the middle which does not make the π-bonding in the aromatic rings conjugate. Because of their limited extent, the aromatic rings only absorb light in the ultraviolet region, and so the compound appears colorless in the 0-8 pH range. However, as the pH increases beyond 8.2, that central carbon becomes part of a double bond becoming sp² hybridized and leaving a p orbital to overlap with the π-bonding in the rings. This makes the three rings conjugate together to form an extended chromophore absorbing longer wavelength visible light to show a fuchsia color. At pH ranges outside 0-12, other molecular structure changes result in other color changes; see Phenolphthalein details.

Common chromophore absorption wavelengths

References

External links