11/29/21, 2:12 PM Chromophore - Wikipedia

Chromophore
A chromophore is the part of a molecule responsible for its color.[2]
The
color that is seen by our eyes is the one not absorbed by the reflecting object
within a certain wavelength 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. Visible light
that hits the chromophore can thus be absorbed by exciting an electron from
its ground state into an excited state. In biological molecules that serve to
capture or detect light energy, the chromophore is the moiety that causes a
conformational change of the molecule when hit by light.
Leaves change color in the Fall
because their chromophores

Contents (chlorophyll molecules) break down

and stop absorbing red and blue
Conjugated pi-bond system chromophores light.[1]

Auxochrome
Halochromism
Common chromophore absorption wavelengths
See also
References
External links

Healthy plants are perceived as

Conjugated pi-bond system chromophores green because chlorophyll absorbs
mainly the blue and red
Just like how two adjacent p-orbitals in a molecule will form a pi-bond, three wavelengths but green light,
or more adjacent p-orbitals in a molecule can form a conjugated pi-system. In reflected by plant structures like cell
a conjugated pi-system, electrons are able to capture certain photons as the walls, is less absorbed.[3]
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 The eleven conjugated double bonds that form
absorb red light. ("Conjugated systems of fewer than eight the chromophore of the β-carotene molecule are
highlighted in red.
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.")[4]

In the conjugated chromophores, the electrons jump between energy levels that are extended pi orbitals, created
by electron clouds like those in aromatic systems. Common examples include retinal (used in the eye to detect
light), various food colorings, fabric dyes (azo compounds), pH indicators, lycopene, 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 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-visible maximum absorption wavelength in organic compounds with conjugated
pi-bond systems.

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Some of these are metal complex chromophores, which contain a metal in a

coordination complex with ligands. Examples are chlorophyll, which is used by
plants for photosynthesis and 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-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.[5][6][7] 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 and urobilin, which exhibit a yellow color.
The porphyrin moieties in our red
Auxochrome blood cells, whose primary function
is to bind iron atoms which capture
oxygen, result in the heme
An auxochrome is a functional group of atoms attached to the chromophore
chromophores which give human
which modifies the ability of the chromophore to absorb light, altering the
blood its red color. Heme is
wavelength or intensity of the absorption.
degraded by the body into biliverdin
(which gives bruises their blue-
Halochromism green color), which in turn is
degraded into bilirubin (which gives
Halochromism occurs when a substance changes color as the pH changes. This patients with jaundice a yellow skin
is a property of pH indicators, whose molecular structure changes upon tone).
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 the human eye, the molecule retinal is a

conjugated chromophore. Retinal begins in an
11-cis-retinal conformation, which, upon capturing
a photon γ (light) of the correct wavelength,
straightens out into an all-trans-retinal
conformation. This conformation change pushes
against an opsin protein in the retina, which
triggers a chemical signaling cascade which can
result in perception of light or images by the
human brain.

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Structure

pH 0-8.2 8.2-12
Conditions acidic or near-neutral basic
Color name colorless pink to fuchsia
Color

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.[8] At pH ranges outside 0-12, other molecular structure changes result in other color
changes; see Phenolphthalein details.

Common chromophore absorption wavelengths

Functional group or Compound Absorption wavelength

Bromophenol Blue (yellow form) 591 nm [9]

Malachite green 617 nm [10] (Green)[11]

Cyanidin 545 nm (Blue)
β-carotene 452 nm (Orange)

See also
Visual phototransduction
Woodward's rules
Chromatophore
Pigment
Photophore, glandular organ
Fluorophore
Litmus
Biological pigment
Spectroscopy

References The International Colour Authority

(ICA) is a private organization
1. Kräutler, Bernhard (26 February 2016). "Breakdown of Chlorophyll in Higher Plants—Phyllobilins
publishing as Abundant,
forecasts about colour trends
Yet Hardly Visible Signs of Ripening, Senescence, and Cell Death" (https://www.ncbi.nlm.nih.gov/pmc/articles/
for the coming seasons, to be used by
PMC4950323). Angew. Chem. Int. Ed. 4882 (55): 4882–4907. doi:10.1002/anie.201508928 (https://doi.org/10.
industry designers. It also awards a Seal
1002%2Fanie.201508928). PMC 4950323 (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4950323).
of Approval that companies may display
PMID 26919572 (https://pubmed.ncbi.nlm.nih.gov/26919572).
in their promotional materials if the
2. IUPAC Gold Book Chromophore (http://goldbook.iupac.org/C01076.html)
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3. Virtanen, Olli; Constantinidou, Emanuella; Tyystjärvi, Esa (2020). "Chlorophyll does not reflect green light –
how to correct a misconception" (https://doi.org/10.1080%2F00219266.2020.1858930). Journal of Biological
Education: 1–8. doi:10.1080/00219266.2020.1858930 (https://doi.org/10.1080%2F00219266.2020.1858930).
4. Lipton, Mark (Jan 31, 2017). "Chapter 1. Electronic Structure and Chemical Bonding" (https://chem.libretexts.or
g/Courses/Purdue/Purdue%3A_Chem_26505%3A_Organic_Chemistry_I_(Lipton)/Chapter_1._Electronic_Stru
cture_and_Chemical_Bonding/1.10%3A_Pi_Conjugation). Purdue: Chem 26505: Organic Chemistry I (Lipton)
(LibreTexts ed.). Purdue University.
5. Gouterman, Martin (2012). "Optical spectra and electronic structure of porphyrins and related rings" (https://bo
oks.google.com/books?id=vuWERW37obgC&pg=PA1). In Dolphin, David (ed.). The Porphyrins V3. Physical
Chemistry, Part A. Elsevier. pp. 1–165. doi:10.1016/B978-0-12-220103-5.50008-8 (https://doi.org/10.1016%2F
B978-0-12-220103-5.50008-8). ISBN 978-0-323-14390-5. NAID 10005456738 (http://ci.nii.ac.jp/naid/10005456
738/en/).
6. Scheer, Hugo (2006). "An Overview of Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics,
Functions and Applications". Chlorophylls and Bacteriochlorophylls. Advances in Photosynthesis and
Respiration. 25. pp. 1–26. doi:10.1007/1-4020-4516-6_1 (https://doi.org/10.1007%2F1-4020-4516-6_1).
ISBN 978-1-4020-4515-8.
7. Shapley, Patricia (2012). "Absorbing light with organic molecules" (http://butane.chem.uiuc.edu/pshapley/GenC
hem2/B2/1.html).
8. UV-Visible Absorption Spectra (http://www.chemguide.co.uk/analysis/uvvisible/theory.html#top)
9. Harris, C. Daniel (2016). Quantitative chemical analysis (9 ed.). New York: Freeman. p. 437.
ISBN 9781464135385.
10. Pretsch, Ernö. (1989). Tables of Spectral Data for Structure Determination of Organic Compounds (https://ww
w.worldcat.org/oclc/851381738). Thomas Clerc, Joseph Seibl, Wilhelm Simon (Second ed.). Berlin,
Heidelberg: Springer Berlin Heidelberg. ISBN 978-3-662-10207-7. OCLC 851381738 (https://www.worldcat.or
g/oclc/851381738).
11. "UV-Vis Spectroscopy | Fundamentals Of UV Visible Spectroscopy" (https://learnbin.net/uv-vis-spectroscopy/).
learnbin.net. Retrieved 2021-11-21.

External links
Causes of Color (http://webexhibits.org/causesofcolor/index.html): physical mechanisms by which color is
generated.
High Speed Nano-Sized Electronics May be Possible with Chromophores (https://web.archive.org/web/200608
05192201/http://www.azonano.com/news.asp?newsID=2538) - Azonano.com

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