Photoisomerization of the compound [[retinal]] in the eye allows for vision.
Photoisomerization of the compound [[retinal]] in the eye allows for vision.
Photoisomerizable substrates have been put to practical use, for instance, in [[pigment]]s for [[CD-RW|rewritable CDs]], [[DVD-RW|DVDs]], and [[3D optical data storage]] solutions. In addition, interest in photoisomerizable molecules has been aimed at molecular devices, such as [[molecular switch]]es,<ref>{{Cite journal |last1=Mammana |first1=A. |year=2011 |title=A Chiroptical Photoswitchable DNA Complex |journal=[[Journal of Physical Chemistry B]] |volume=115 |issue=40 |pages=11581–11587 |doi=10.1021/jp205893y |pmid=21879715 |display-authors=etal|url=https://pure.rug.nl/ws/files/10462706/2011JPhysChemBMammanaSupp.pdf |hdl=11370/cca715c8-861f-4500-943f-028c95e8e55e |s2cid=33375716 |hdl-access=free }}</ref><ref>{{cite journal | last1=Mokdad | first1 = A | last2 = Belof | first2 = J | last3 = Yi | first3 = S | last4 = Shuler | first4 = S | last5 = McLaughlin | first5 = M | last6 = Space | first6 = B | last7 = Larsen | first7 = R | title = Photophysical Studies of the Trans to Cis Isomerization of the Push−Pull Molecule: 1-(Pyridin-4-yl)-2-(N-methylpyrrol-2-yl)ethene (mepepy) | journal=[[Journal of Physical Chemistry B]] | volume = 112 | issue = 36 | pages = 8310–8315 | year = 2008 | doi = 10.1021/jp803268r | pmid = 18700732 | bibcode = 2008JPCA..112.8310M }}</ref> [[molecular motor]]s,<ref>{{Cite journal |last1=Vachon |first1=J. |year=2014 |title=An ultrafast surface-bound photo-active molecular motor |journal=[[Photochemical and Photobiological Sciences]] |volume=13 |issue=2 |pages=241–246 |doi=10.1039/C3PP50208B |pmid=24096390 |s2cid=23165784 |display-authors=etal|url=http://dare.uva.nl/personal/pure/en/publications/an-ultrafast-surfacebound-photoactive-molecular-motor(ca92afa2-9b98-44e8-b06c-c29c41da008d).html }}</ref> and [[molecular electronics]].
Photoisomerizable substrates have been put to practical use, for instance, in [[pigment]]s for [[CD-RW|rewritable CDs]], [[DVD-RW|DVDs]], and [[3D optical data storage]] solutions. In addition, interest in photoisomerizable molecules has been aimed at molecular devices, such as [[molecular switch]]es,<ref>{{Cite journal |last1=Mammana |first1=A. |year=2011 |title=A Chiroptical Photoswitchable DNA Complex |journal=[[Journal of Physical Chemistry B]] |volume=115 |issue=40 |pages=11581–11587 |doi=10.1021/jp205893y |pmid=21879715 |display-authors=etal|url=https://pure.rug.nl/ws/files/10462706/2011JPhysChemBMammanaSupp.pdf |hdl=11370/cca715c8-861f-4500-943f-028c95e8e55e |s2cid=33375716 |hdl-access=free }}</ref><ref>{{cite journal | last1=Mokdad | first1 = A | last2 = Belof | first2 = J | last3 = Yi | first3 = S | last4 = Shuler | first4 = S | last5 = McLaughlin | first5 = M | last6 = Space | first6 = B | last7 = Larsen | first7 = R | title = Photophysical Studies of the Trans to Cis Isomerization of the Push−Pull Molecule: 1-(Pyridin-4-yl)-2-(N-methylpyrrol-2-yl)ethene (mepepy) | journal=[[Journal of Physical Chemistry B]] | volume = 112 | issue = 36 | pages = 8310–8315 | year = 2008 | doi = 10.1021/jp803268r | pmid = 18700732 | bibcode = 2008JPCA..112.8310M }}</ref> [[molecular motor]]s,<ref>{{Cite journal |last1=Vachon |first1=J. |year=2014 |title=An ultrafast surface-bound photo-active molecular motor |journal=[[Photochemical and Photobiological Sciences]] |volume=13 |issue=2 |pages=241–246 |doi=10.1039/C3PP50208B |pmid=24096390 |bibcode=2014PhPhS..13..241V |s2cid=23165784 |display-authors=etal|url=http://dare.uva.nl/personal/pure/en/publications/an-ultrafast-surfacebound-photoactive-molecular-motor(ca92afa2-9b98-44e8-b06c-c29c41da008d).html }}</ref> and [[molecular electronics]].
Another class of device that uses the photoisomerization process is as an additive in [[liquid crystals]] to change their linear and nonlinear properties.<ref>{{cite journal |last1=Janossy |first1=I. |last2=Szabados |first2=L. |title=Optical reorientation of nematic liquid crystals in the presence of photoisomerization |journal=Physical Review E |date=1 October 1998 |volume=58 |issue=4 |page=4598 |doi=10.1103/PhysRevE.58.4598|bibcode=1998PhRvE..58.4598J |s2cid=26508261 }}</ref> Due to the photoisomerization is possible to induce a molecular reorientation in the liquid crystal bulk, which is used in [[holography]],<ref>{{cite journal |last1=Chen |first1=Alan G |last2=Brady |first2=David J |title=Real-time holography in azo-dye-doped liquid crystals |journal=Optics Letters |date=1992 |volume=17 |issue=6 |pages=441–3 |doi=10.1364/OL.17.000441|pmid=19784354 |bibcode=1992OptL...17..441C |s2cid=20923350 }}</ref> as [[spatial filter]]<ref>{{cite journal |last1=Kato |first1=Jun-ichi |last2=Yamaguchi |first2=Ichirou |title=Nonlinear spatial filtering with a dye-doped liquid-crystal cell |journal=Optics Letters |date=1996 |volume=21 |issue=11 |pages=767–769 |doi=10.1364/OL.21.000767|pmid=19876152 |bibcode=1996OptL...21..767K }}</ref> or optical switching.<ref>{{cite journal |last1=Maly |first1=Kenneth E |last2=Wand |first2=Michael D |title=Bistable ferroelectric liquid crystal photoswitch triggered by a dithienylethene dopant |journal=Journal of the American Chemical Society |date=2002 |volume=124 |issue=27 |pages=7898–7899 |doi=10.1364/OPEX.13.002358|pmid=19495125 |doi-access=free}}</ref>
Another class of device that uses the photoisomerization process is as an additive in [[liquid crystals]] to change their linear and nonlinear properties.<ref>{{cite journal |last1=Janossy |first1=I. |last2=Szabados |first2=L. |title=Optical reorientation of nematic liquid crystals in the presence of photoisomerization |journal=Physical Review E |date=1 October 1998 |volume=58 |issue=4 |page=4598 |doi=10.1103/PhysRevE.58.4598|bibcode=1998PhRvE..58.4598J |s2cid=26508261 }}</ref> Due to the photoisomerization is possible to induce a molecular reorientation in the liquid crystal bulk, which is used in [[holography]],<ref>{{cite journal |last1=Chen |first1=Alan G |last2=Brady |first2=David J |title=Real-time holography in azo-dye-doped liquid crystals |journal=Optics Letters |date=1992 |volume=17 |issue=6 |pages=441–3 |doi=10.1364/OL.17.000441|pmid=19784354 |bibcode=1992OptL...17..441C |s2cid=20923350 }}</ref> as [[spatial filter]]<ref>{{cite journal |last1=Kato |first1=Jun-ichi |last2=Yamaguchi |first2=Ichirou |title=Nonlinear spatial filtering with a dye-doped liquid-crystal cell |journal=Optics Letters |date=1996 |volume=21 |issue=11 |pages=767–769 |doi=10.1364/OL.21.000767|pmid=19876152 |bibcode=1996OptL...21..767K }}</ref> or optical switching.<ref>{{cite journal |last1=Maly |first1=Kenneth E |last2=Wand |first2=Michael D |title=Bistable ferroelectric liquid crystal photoswitch triggered by a dithienylethene dopant |journal=Journal of the American Chemical Society |date=2002 |volume=124 |issue=27 |pages=7898–7899 |doi=10.1364/OPEX.13.002358|pmid=19495125 |doi-access=free}}</ref>
In chemistry, photoisomerization is a form of isomerization induced by photoexcitation.[2] Both reversible and irreversible photoisomerizations are known for photoswitchable compounds. The term "photoisomerization" usually, however, refers to a reversible process.
Another class of device that uses the photoisomerization process is as an additive in liquid crystals to change their linear and nonlinear properties.[6] Due to the photoisomerization is possible to induce a molecular reorientation in the liquid crystal bulk, which is used in holography,[7] as spatial filter[8] or optical switching.[9]
File:Methyl red.svgMethyl red molecule, a common azo dye used in liquid crystal doping
In the presence of a catalyst, norbornadiene converts to quadricyclane via ~300nm UV radiation. When converted back to norbornadiene, quadryicyclane’s ring strain energy is liberated in the form of heat (ΔH = −89 kJ/mol). This reaction has been proposed to store solar energy (photoswitchs).[12]
Photoisomerization behavior can be roughly categorized into several classes. Two major classes are trans–cis (or E–Z) conversion, and open-closed ring transition. Examples of the former include stilbene and azobenzene. This type of compounds has a double bond, and rotation or inversion around the double bond affords isomerization between the two states.[13] Examples of the latter include fulgide and diarylethene. This type of compounds undergoes bond cleavage and bond creation upon irradiation with particular wavelengths of light. Still another class is the di-π-methane rearrangement.
Coordination chemistry
Many complexes are often photosensitive and many of these complexes undergo photoisomerization.[14] One case is the conversion of the colorless cis-bis(triphenylphosphine)platinum chloride to the yellow trans isomer.
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