Synthesis of Vinylnaphthofurans and NMR Analysis of their Photoswitching

An easy synthesis of photochromic vinylnaphthofurans by the acid‐catalyzed one‐pot reaction of naphthols with but‐2‐yne‐1,4‐diols is described. These uncolored polyaromatic compounds are activated by UV light, at room temperature, and converted through a stilbene‐type electrocyclization into a therm...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2021-04, Vol.2021 (13), p.1979-1988
Main Authors: Graça, Vânia, Berthet, Jérôme, Sousa, Céu M., Delbaere, Stephanie, Coelho, Paulo J.
Format: Article
Language:English
Subjects:
Chemical Sciences
Diols
Electrocyclization
Naphthofurans
NMR
Nuclear magnetic resonance
One-pot synthesis
Photochromism
Room temperature
Stilbene
Thermal stability
Ultraviolet radiation
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-c3914-877ce0d31751eeb2805911b5788de2fd407b3f0fe1c161df3ff02ead52b1bea3
cites cdi_FETCH-LOGICAL-c3914-877ce0d31751eeb2805911b5788de2fd407b3f0fe1c161df3ff02ead52b1bea3
container_end_page 1988
container_issue 13
container_start_page 1979
container_title European journal of organic chemistry
container_volume 2021
creator Graça, Vânia
Berthet, Jérôme
Sousa, Céu M.
Delbaere, Stephanie
Coelho, Paulo J.
description An easy synthesis of photochromic vinylnaphthofurans by the acid‐catalyzed one‐pot reaction of naphthols with but‐2‐yne‐1,4‐diols is described. These uncolored polyaromatic compounds are activated by UV light, at room temperature, and converted through a stilbene‐type electrocyclization into a thermally stable orange species, which can be switched back using visible light. The behavior of these photoswitches was elucidated using NMR, which allowed to identify the photoisomers and some side‐products, formed after prolonged UV irradiation. An easy synthesis of photochromic vinylnaphthofurans by the acid‐catalyzed one‐pot reaction of naphthols with but‐2‐yne‐1,4‐diols is described. These polyaromatic compounds switch between uncolored (Vis) and colored (UV) states at room temperature. NMR analysis of irradiated solutions allowed to identify the photoisomers and some side‐products.
doi_str_mv 10.1002/ejoc.202100114
format article
fullrecord <record><control><sourceid>proquest_hal_p</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_04341817v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2543729108</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3914-877ce0d31751eeb2805911b5788de2fd407b3f0fe1c161df3ff02ead52b1bea3</originalsourceid><addsrcrecordid>eNqFkM9LwzAcxYsoOKdXzwVPHjq_36Rdm-MY6pTpRId4C2mb2IzazKRz9L83o2MePX1_8HkP3guCS4QRApAbuTLFiADxB2J8FAwQGItgzODY7zGNI2T04zQ4c24FAGw8xkEwe-uatpJOu9Co8F03Xd2IddVWRm2saFwomjJ8fnoNJ42ouz3mBdqGL5Vpjdvqtqh083kenChRO3mxn8NgeXe7nM6i-eL-YTqZRwVlGEdZmhYSSoppglLmJIOEIeZJmmWlJKqMIc2pAiWxwDGWiioFRIoyITnmUtBhcN3bVqLma6u_hO24EZrPJnO--4EPihmmP-jZq55dW_O9ka7lK7OxPofjJIlpShhC5qlRTxXWOGelOtgi8F2xfFcsPxTrBawXbHUtu39ofvu4mP5pfwE1JHwP</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2543729108</pqid></control><display><type>article</type><title>Synthesis of Vinylnaphthofurans and NMR Analysis of their Photoswitching</title><source>Wiley-Blackwell Read &amp; Publish Collection</source><creator>Graça, Vânia ; Berthet, Jérôme ; Sousa, Céu M. ; Delbaere, Stephanie ; Coelho, Paulo J.</creator><creatorcontrib>Graça, Vânia ; Berthet, Jérôme ; Sousa, Céu M. ; Delbaere, Stephanie ; Coelho, Paulo J.</creatorcontrib><description>An easy synthesis of photochromic vinylnaphthofurans by the acid‐catalyzed one‐pot reaction of naphthols with but‐2‐yne‐1,4‐diols is described. These uncolored polyaromatic compounds are activated by UV light, at room temperature, and converted through a stilbene‐type electrocyclization into a thermally stable orange species, which can be switched back using visible light. The behavior of these photoswitches was elucidated using NMR, which allowed to identify the photoisomers and some side‐products, formed after prolonged UV irradiation. An easy synthesis of photochromic vinylnaphthofurans by the acid‐catalyzed one‐pot reaction of naphthols with but‐2‐yne‐1,4‐diols is described. These polyaromatic compounds switch between uncolored (Vis) and colored (UV) states at room temperature. NMR analysis of irradiated solutions allowed to identify the photoisomers and some side‐products.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202100114</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Chemical Sciences ; Diols ; Electrocyclization ; Naphthofurans ; NMR ; Nuclear magnetic resonance ; One-pot synthesis ; Photochromism ; Room temperature ; Stilbene ; Thermal stability ; Ultraviolet radiation</subject><ispartof>European journal of organic chemistry, 2021-04, Vol.2021 (13), p.1979-1988</ispartof><rights>2021 Wiley‐VCH GmbH</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3914-877ce0d31751eeb2805911b5788de2fd407b3f0fe1c161df3ff02ead52b1bea3</citedby><cites>FETCH-LOGICAL-c3914-877ce0d31751eeb2805911b5788de2fd407b3f0fe1c161df3ff02ead52b1bea3</cites><orcidid>0000-0003-4328-5694</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,27924,27925</link.rule.ids><backlink>$$Uhttps://hal.science/hal-04341817$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Graça, Vânia</creatorcontrib><creatorcontrib>Berthet, Jérôme</creatorcontrib><creatorcontrib>Sousa, Céu M.</creatorcontrib><creatorcontrib>Delbaere, Stephanie</creatorcontrib><creatorcontrib>Coelho, Paulo J.</creatorcontrib><title>Synthesis of Vinylnaphthofurans and NMR Analysis of their Photoswitching</title><title>European journal of organic chemistry</title><description>An easy synthesis of photochromic vinylnaphthofurans by the acid‐catalyzed one‐pot reaction of naphthols with but‐2‐yne‐1,4‐diols is described. These uncolored polyaromatic compounds are activated by UV light, at room temperature, and converted through a stilbene‐type electrocyclization into a thermally stable orange species, which can be switched back using visible light. The behavior of these photoswitches was elucidated using NMR, which allowed to identify the photoisomers and some side‐products, formed after prolonged UV irradiation. An easy synthesis of photochromic vinylnaphthofurans by the acid‐catalyzed one‐pot reaction of naphthols with but‐2‐yne‐1,4‐diols is described. These polyaromatic compounds switch between uncolored (Vis) and colored (UV) states at room temperature. NMR analysis of irradiated solutions allowed to identify the photoisomers and some side‐products.</description><subject>Chemical Sciences</subject><subject>Diols</subject><subject>Electrocyclization</subject><subject>Naphthofurans</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>One-pot synthesis</subject><subject>Photochromism</subject><subject>Room temperature</subject><subject>Stilbene</subject><subject>Thermal stability</subject><subject>Ultraviolet radiation</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkM9LwzAcxYsoOKdXzwVPHjq_36Rdm-MY6pTpRId4C2mb2IzazKRz9L83o2MePX1_8HkP3guCS4QRApAbuTLFiADxB2J8FAwQGItgzODY7zGNI2T04zQ4c24FAGw8xkEwe-uatpJOu9Co8F03Xd2IddVWRm2saFwomjJ8fnoNJ42ouz3mBdqGL5Vpjdvqtqh083kenChRO3mxn8NgeXe7nM6i-eL-YTqZRwVlGEdZmhYSSoppglLmJIOEIeZJmmWlJKqMIc2pAiWxwDGWiioFRIoyITnmUtBhcN3bVqLma6u_hO24EZrPJnO--4EPihmmP-jZq55dW_O9ka7lK7OxPofjJIlpShhC5qlRTxXWOGelOtgi8F2xfFcsPxTrBawXbHUtu39ofvu4mP5pfwE1JHwP</recordid><startdate>20210408</startdate><enddate>20210408</enddate><creator>Graça, Vânia</creator><creator>Berthet, Jérôme</creator><creator>Sousa, Céu M.</creator><creator>Delbaere, Stephanie</creator><creator>Coelho, Paulo J.</creator><general>Wiley Subscription Services, Inc</general><general>Wiley-VCH Verlag</general><scope>AAYXX</scope><scope>CITATION</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0003-4328-5694</orcidid></search><sort><creationdate>20210408</creationdate><title>Synthesis of Vinylnaphthofurans and NMR Analysis of their Photoswitching</title><author>Graça, Vânia ; Berthet, Jérôme ; Sousa, Céu M. ; Delbaere, Stephanie ; Coelho, Paulo J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3914-877ce0d31751eeb2805911b5788de2fd407b3f0fe1c161df3ff02ead52b1bea3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Chemical Sciences</topic><topic>Diols</topic><topic>Electrocyclization</topic><topic>Naphthofurans</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>One-pot synthesis</topic><topic>Photochromism</topic><topic>Room temperature</topic><topic>Stilbene</topic><topic>Thermal stability</topic><topic>Ultraviolet radiation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Graça, Vânia</creatorcontrib><creatorcontrib>Berthet, Jérôme</creatorcontrib><creatorcontrib>Sousa, Céu M.</creatorcontrib><creatorcontrib>Delbaere, Stephanie</creatorcontrib><creatorcontrib>Coelho, Paulo J.</creatorcontrib><collection>CrossRef</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Graça, Vânia</au><au>Berthet, Jérôme</au><au>Sousa, Céu M.</au><au>Delbaere, Stephanie</au><au>Coelho, Paulo J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Vinylnaphthofurans and NMR Analysis of their Photoswitching</atitle><jtitle>European journal of organic chemistry</jtitle><date>2021-04-08</date><risdate>2021</risdate><volume>2021</volume><issue>13</issue><spage>1979</spage><epage>1988</epage><pages>1979-1988</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>An easy synthesis of photochromic vinylnaphthofurans by the acid‐catalyzed one‐pot reaction of naphthols with but‐2‐yne‐1,4‐diols is described. These uncolored polyaromatic compounds are activated by UV light, at room temperature, and converted through a stilbene‐type electrocyclization into a thermally stable orange species, which can be switched back using visible light. The behavior of these photoswitches was elucidated using NMR, which allowed to identify the photoisomers and some side‐products, formed after prolonged UV irradiation. An easy synthesis of photochromic vinylnaphthofurans by the acid‐catalyzed one‐pot reaction of naphthols with but‐2‐yne‐1,4‐diols is described. These polyaromatic compounds switch between uncolored (Vis) and colored (UV) states at room temperature. NMR analysis of irradiated solutions allowed to identify the photoisomers and some side‐products.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.202100114</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0003-4328-5694</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1434-193X
ispartof European journal of organic chemistry, 2021-04, Vol.2021 (13), p.1979-1988
issn 1434-193X
1099-0690
language eng
recordid cdi_hal_primary_oai_HAL_hal_04341817v1
source Wiley-Blackwell Read & Publish Collection
subjects Chemical Sciences
Diols
Electrocyclization
Naphthofurans
NMR
Nuclear magnetic resonance
One-pot synthesis
Photochromism
Room temperature
Stilbene
Thermal stability
Ultraviolet radiation
title Synthesis of Vinylnaphthofurans and NMR Analysis of their Photoswitching
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-04T02%3A39%3A48IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_hal_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%20Vinylnaphthofurans%20and%20NMR%20Analysis%20of%20their%20Photoswitching&rft.jtitle=European%20journal%20of%20organic%20chemistry&rft.au=Gra%C3%A7a,%20V%C3%A2nia&rft.date=2021-04-08&rft.volume=2021&rft.issue=13&rft.spage=1979&rft.epage=1988&rft.pages=1979-1988&rft.issn=1434-193X&rft.eissn=1099-0690&rft_id=info:doi/10.1002/ejoc.202100114&rft_dat=%3Cproquest_hal_p%3E2543729108%3C/proquest_hal_p%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c3914-877ce0d31751eeb2805911b5788de2fd407b3f0fe1c161df3ff02ead52b1bea3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2543729108&rft_id=info:pmid/&rfr_iscdi=true