Photochromic derivatives of indigo: historical overview of development, challenges and applications

The importance of indigo dyes is constantly increasing with the evolution of novel textile materials and photochromic material technologies. The aim of this review article is to provide a comprehensive overview of the development of photochromic indigo derivatives from the first report on the photoc...

Full description

Saved in:
Bibliographic Details
Published in:Beilstein journal of organic chemistry 2024-02, Vol.20 (1), p.228-242
Main Authors: Kaplan, Gökhan, Seferoğlu, Zeynel, Berdnikova, Daria V
Format: Article
Language:English
Subjects:
Chemistry
e–z isomerization
indigoid dyes
photochemistry
photophysics
photoswitching
Review
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c445t-532bdcdc77506f1383a833e71b1ba226debac07ae1a8ebeb915318e0026f34bc3
cites cdi_FETCH-LOGICAL-c445t-532bdcdc77506f1383a833e71b1ba226debac07ae1a8ebeb915318e0026f34bc3
container_end_page 242
container_issue 1
container_start_page 228
container_title Beilstein journal of organic chemistry
container_volume 20
creator Kaplan, Gökhan
Seferoğlu, Zeynel
Berdnikova, Daria V
description The importance of indigo dyes is constantly increasing with the evolution of novel textile materials and photochromic material technologies. The aim of this review article is to provide a comprehensive overview of the development of photochromic indigo derivatives from the first report on the photochromic -diacetylindigo in 1954 until now. We begin with the list of historical milestones in the development of photochromic indigo derivatives. Further, we provide a brief description of the synthetic procedures utilised to obtain indigo and its derivatives, outline the structural peculiarities, photophysical and photochemical properties of indigo and proceed with the detailed discussion of the photochromic indigo derivatives. Finally, we highlight the photochromism of the structural isomers of indigo (isoindigo and indirubin) and provide an overview of prospective applications of indigo photoswitches.
doi_str_mv 10.3762/bjoc.20.23
format article
fullrecord <record><control><sourceid>proquest_doaj_</sourceid><recordid>TN_cdi_doaj_primary_oai_doaj_org_article_7d1c72ddbbad43c7afaa2b41d6087d3d</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><doaj_id>oai_doaj_org_article_7d1c72ddbbad43c7afaa2b41d6087d3d</doaj_id><sourcerecordid>2926521369</sourcerecordid><originalsourceid>FETCH-LOGICAL-c445t-532bdcdc77506f1383a833e71b1ba226debac07ae1a8ebeb915318e0026f34bc3</originalsourceid><addsrcrecordid>eNpVkU9v1DAQxS1ERUvhwgdAOaKqu_hPYme5IFQBrVQJDnC2xvZk45UTBzubqt8eL1uq9uSR581v3ugR8o7RtVCSfzS7aNecrrl4Qc5YK-mqERv18kl9Sl7nvKO0ppLKV-RUtKLhVNEzYn_2cY62T3HwtnKY_AKzXzBXsav86Pw2fqp6n-eYvIVQxQXT4vHu0Ha4YIjTgON8WdkeQsBxWyZhdBVMUygDs49jfkNOOggZ3z685-T3t6-_rq5Xtz--31x9uV3Zum7mYpQbZ51VqqGyY8UjtEKgYoYZ4Fw6NGCpAmTQokGzYY1gLVLKZSdqY8U5uTlyXYSdnpIfIN3rCF7_-4hpqyHN3gbUyjGruHPGgKuFVdABcFMzJ2mrnHCF9fnImvZmQGfLjQnCM-jzzuh7vY2LZrSVnAlVCB8eCCn-2WOe9eCzxRBgxLjPmm-4bIpSbor04ii1KeacsHvcw6g-RKwPEWtONRdF_P6ps0fp_0zFX-kFpfo</addsrcrecordid><sourcetype>Open Website</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2926521369</pqid></control><display><type>article</type><title>Photochromic derivatives of indigo: historical overview of development, challenges and applications</title><source>Publicly Available Content Database</source><source>PubMed Central</source><creator>Kaplan, Gökhan ; Seferoğlu, Zeynel ; Berdnikova, Daria V</creator><creatorcontrib>Kaplan, Gökhan ; Seferoğlu, Zeynel ; Berdnikova, Daria V</creatorcontrib><description>The importance of indigo dyes is constantly increasing with the evolution of novel textile materials and photochromic material technologies. The aim of this review article is to provide a comprehensive overview of the development of photochromic indigo derivatives from the first report on the photochromic -diacetylindigo in 1954 until now. We begin with the list of historical milestones in the development of photochromic indigo derivatives. Further, we provide a brief description of the synthetic procedures utilised to obtain indigo and its derivatives, outline the structural peculiarities, photophysical and photochemical properties of indigo and proceed with the detailed discussion of the photochromic indigo derivatives. Finally, we highlight the photochromism of the structural isomers of indigo (isoindigo and indirubin) and provide an overview of prospective applications of indigo photoswitches.</description><identifier>ISSN: 1860-5397</identifier><identifier>EISSN: 1860-5397</identifier><identifier>DOI: 10.3762/bjoc.20.23</identifier><identifier>PMID: 38352070</identifier><language>eng</language><publisher>Germany: Beilstein-Institut</publisher><subject>Chemistry ; e–z isomerization ; indigoid dyes ; photochemistry ; photophysics ; photoswitching ; Review</subject><ispartof>Beilstein journal of organic chemistry, 2024-02, Vol.20 (1), p.228-242</ispartof><rights>Copyright © 2024, Kaplan et al.</rights><rights>Copyright © 2024, Kaplan et al. 2024 Kaplan et al.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c445t-532bdcdc77506f1383a833e71b1ba226debac07ae1a8ebeb915318e0026f34bc3</citedby><cites>FETCH-LOGICAL-c445t-532bdcdc77506f1383a833e71b1ba226debac07ae1a8ebeb915318e0026f34bc3</cites><orcidid>0000-0001-8526-7051 ; 0000-0002-0787-5753 ; 0000-0002-1028-7231</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10862137/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10862137/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,881,27901,27902,36990,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38352070$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kaplan, Gökhan</creatorcontrib><creatorcontrib>Seferoğlu, Zeynel</creatorcontrib><creatorcontrib>Berdnikova, Daria V</creatorcontrib><title>Photochromic derivatives of indigo: historical overview of development, challenges and applications</title><title>Beilstein journal of organic chemistry</title><addtitle>Beilstein J Org Chem</addtitle><description>The importance of indigo dyes is constantly increasing with the evolution of novel textile materials and photochromic material technologies. The aim of this review article is to provide a comprehensive overview of the development of photochromic indigo derivatives from the first report on the photochromic -diacetylindigo in 1954 until now. We begin with the list of historical milestones in the development of photochromic indigo derivatives. Further, we provide a brief description of the synthetic procedures utilised to obtain indigo and its derivatives, outline the structural peculiarities, photophysical and photochemical properties of indigo and proceed with the detailed discussion of the photochromic indigo derivatives. Finally, we highlight the photochromism of the structural isomers of indigo (isoindigo and indirubin) and provide an overview of prospective applications of indigo photoswitches.</description><subject>Chemistry</subject><subject>e–z isomerization</subject><subject>indigoid dyes</subject><subject>photochemistry</subject><subject>photophysics</subject><subject>photoswitching</subject><subject>Review</subject><issn>1860-5397</issn><issn>1860-5397</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>DOA</sourceid><recordid>eNpVkU9v1DAQxS1ERUvhwgdAOaKqu_hPYme5IFQBrVQJDnC2xvZk45UTBzubqt8eL1uq9uSR581v3ugR8o7RtVCSfzS7aNecrrl4Qc5YK-mqERv18kl9Sl7nvKO0ppLKV-RUtKLhVNEzYn_2cY62T3HwtnKY_AKzXzBXsav86Pw2fqp6n-eYvIVQxQXT4vHu0Ha4YIjTgON8WdkeQsBxWyZhdBVMUygDs49jfkNOOggZ3z685-T3t6-_rq5Xtz--31x9uV3Zum7mYpQbZ51VqqGyY8UjtEKgYoYZ4Fw6NGCpAmTQokGzYY1gLVLKZSdqY8U5uTlyXYSdnpIfIN3rCF7_-4hpqyHN3gbUyjGruHPGgKuFVdABcFMzJ2mrnHCF9fnImvZmQGfLjQnCM-jzzuh7vY2LZrSVnAlVCB8eCCn-2WOe9eCzxRBgxLjPmm-4bIpSbor04ii1KeacsHvcw6g-RKwPEWtONRdF_P6ps0fp_0zFX-kFpfo</recordid><startdate>20240207</startdate><enddate>20240207</enddate><creator>Kaplan, Gökhan</creator><creator>Seferoğlu, Zeynel</creator><creator>Berdnikova, Daria V</creator><general>Beilstein-Institut</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0001-8526-7051</orcidid><orcidid>https://orcid.org/0000-0002-0787-5753</orcidid><orcidid>https://orcid.org/0000-0002-1028-7231</orcidid></search><sort><creationdate>20240207</creationdate><title>Photochromic derivatives of indigo: historical overview of development, challenges and applications</title><author>Kaplan, Gökhan ; Seferoğlu, Zeynel ; Berdnikova, Daria V</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c445t-532bdcdc77506f1383a833e71b1ba226debac07ae1a8ebeb915318e0026f34bc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Chemistry</topic><topic>e–z isomerization</topic><topic>indigoid dyes</topic><topic>photochemistry</topic><topic>photophysics</topic><topic>photoswitching</topic><topic>Review</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kaplan, Gökhan</creatorcontrib><creatorcontrib>Seferoğlu, Zeynel</creatorcontrib><creatorcontrib>Berdnikova, Daria V</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Beilstein journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kaplan, Gökhan</au><au>Seferoğlu, Zeynel</au><au>Berdnikova, Daria V</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photochromic derivatives of indigo: historical overview of development, challenges and applications</atitle><jtitle>Beilstein journal of organic chemistry</jtitle><addtitle>Beilstein J Org Chem</addtitle><date>2024-02-07</date><risdate>2024</risdate><volume>20</volume><issue>1</issue><spage>228</spage><epage>242</epage><pages>228-242</pages><issn>1860-5397</issn><eissn>1860-5397</eissn><abstract>The importance of indigo dyes is constantly increasing with the evolution of novel textile materials and photochromic material technologies. The aim of this review article is to provide a comprehensive overview of the development of photochromic indigo derivatives from the first report on the photochromic -diacetylindigo in 1954 until now. We begin with the list of historical milestones in the development of photochromic indigo derivatives. Further, we provide a brief description of the synthetic procedures utilised to obtain indigo and its derivatives, outline the structural peculiarities, photophysical and photochemical properties of indigo and proceed with the detailed discussion of the photochromic indigo derivatives. Finally, we highlight the photochromism of the structural isomers of indigo (isoindigo and indirubin) and provide an overview of prospective applications of indigo photoswitches.</abstract><cop>Germany</cop><pub>Beilstein-Institut</pub><pmid>38352070</pmid><doi>10.3762/bjoc.20.23</doi><tpages>15</tpages><orcidid>https://orcid.org/0000-0001-8526-7051</orcidid><orcidid>https://orcid.org/0000-0002-0787-5753</orcidid><orcidid>https://orcid.org/0000-0002-1028-7231</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1860-5397
ispartof Beilstein journal of organic chemistry, 2024-02, Vol.20 (1), p.228-242
issn 1860-5397
1860-5397
language eng
recordid cdi_doaj_primary_oai_doaj_org_article_7d1c72ddbbad43c7afaa2b41d6087d3d
source Publicly Available Content Database; PubMed Central
subjects Chemistry
e–z isomerization
indigoid dyes
photochemistry
photophysics
photoswitching
Review
title Photochromic derivatives of indigo: historical overview of development, challenges and applications
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-30T22%3A54%3A59IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_doaj_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Photochromic%20derivatives%20of%20indigo:%20historical%20overview%20of%20development,%20challenges%20and%20applications&rft.jtitle=Beilstein%20journal%20of%20organic%20chemistry&rft.au=Kaplan,%20G%C3%B6khan&rft.date=2024-02-07&rft.volume=20&rft.issue=1&rft.spage=228&rft.epage=242&rft.pages=228-242&rft.issn=1860-5397&rft.eissn=1860-5397&rft_id=info:doi/10.3762/bjoc.20.23&rft_dat=%3Cproquest_doaj_%3E2926521369%3C/proquest_doaj_%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c445t-532bdcdc77506f1383a833e71b1ba226debac07ae1a8ebeb915318e0026f34bc3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2926521369&rft_id=info:pmid/38352070&rfr_iscdi=true