3-Piperazinyl propenylidene indolone merocyanines: consecutive three-component synthesis and electronic properties of solid-state luminophores with AIE properties

A series of twelve 3-piperazinyl propenylidene indolone merocyanines was synthesized in a one-pot fashion using a consecutive three-component insertion-coupling-Michael addition sequence. Physical-organic treatment of the absorption data of a consanguineous series of this library allows semiquantita...

Full description

Saved in:
Bibliographic Details
Published in:Materials chemistry frontiers 2017-10, Vol.1 (10), p.2013-2026
Main Authors: Denißen, Melanie, Nirmalananthan, Nithiya, Behnke, Thomas, Hoffmann, Katrin, Resch-Genger, Ute, Müller, Thomas J. J.
Format: Article
Language:English
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-c272t-9753ff67b99a9db339720b9d77138b4c47e3c4dd161a4226a1ff580334557a183
cites cdi_FETCH-LOGICAL-c272t-9753ff67b99a9db339720b9d77138b4c47e3c4dd161a4226a1ff580334557a183
container_end_page 2026
container_issue 10
container_start_page 2013
container_title Materials chemistry frontiers
container_volume 1
creator Denißen, Melanie
Nirmalananthan, Nithiya
Behnke, Thomas
Hoffmann, Katrin
Resch-Genger, Ute
Müller, Thomas J. J.
description A series of twelve 3-piperazinyl propenylidene indolone merocyanines was synthesized in a one-pot fashion using a consecutive three-component insertion-coupling-Michael addition sequence. Physical-organic treatment of the absorption data of a consanguineous series of this library allows semiquantitative Linear Free Energy Relationships (LFERs) to be established and confirmation of the positive absorption solvatochromicity. All Boc-substituted piperazinyl merocyanines display aggregation induced emission (AIE), which was corroborated for two solvent systems. In particular, crystallization-induced emission enhancement (CIEE) induced by ultrasonication could be shown for a model chromophore by confocal laser scanning microscopy (CLSM).
doi_str_mv 10.1039/C7QM00198C
format article
fullrecord <record><control><sourceid>crossref</sourceid><recordid>TN_cdi_crossref_primary_10_1039_C7QM00198C</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>10_1039_C7QM00198C</sourcerecordid><originalsourceid>FETCH-LOGICAL-c272t-9753ff67b99a9db339720b9d77138b4c47e3c4dd161a4226a1ff580334557a183</originalsourceid><addsrcrecordid>eNpNkM1KxDAUhYMoOIyz8QmyFqr5aZvG3VBGHRhRQdclTW9ppE1KklHq4_ikVkZwVveD-3EOHIQuKbmmhMubUrw8EkJlUZ6gBSMZS2jGxekRn6NVCO9kloRgnNAF-ubJsxnBqy9jpx6P3o0wg2nAAja2cb2bYQDv9KSssRBusXY2gN5H8wE4dh4g0W4YZ89GHCYbOwgmYGUbDD3o6J01-pDso4GAXYuDmyuSEFUE3O8HY93YOT__Pk3s8Hq7OfIv0Fmr-gCrv7tEb3eb1_Ih2T3db8v1LtFMsJhIkfG2zUUtpZJNzbkUjNSyEYLyok51KoDrtGloTlXKWK5o22YF4TzNMqFowZfo6pCrvQvBQ1uN3gzKTxUl1e_A1f_A_AdbenJo</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>3-Piperazinyl propenylidene indolone merocyanines: consecutive three-component synthesis and electronic properties of solid-state luminophores with AIE properties</title><source>Royal Society of Chemistry Journals</source><creator>Denißen, Melanie ; Nirmalananthan, Nithiya ; Behnke, Thomas ; Hoffmann, Katrin ; Resch-Genger, Ute ; Müller, Thomas J. J.</creator><creatorcontrib>Denißen, Melanie ; Nirmalananthan, Nithiya ; Behnke, Thomas ; Hoffmann, Katrin ; Resch-Genger, Ute ; Müller, Thomas J. J.</creatorcontrib><description>A series of twelve 3-piperazinyl propenylidene indolone merocyanines was synthesized in a one-pot fashion using a consecutive three-component insertion-coupling-Michael addition sequence. Physical-organic treatment of the absorption data of a consanguineous series of this library allows semiquantitative Linear Free Energy Relationships (LFERs) to be established and confirmation of the positive absorption solvatochromicity. All Boc-substituted piperazinyl merocyanines display aggregation induced emission (AIE), which was corroborated for two solvent systems. In particular, crystallization-induced emission enhancement (CIEE) induced by ultrasonication could be shown for a model chromophore by confocal laser scanning microscopy (CLSM).</description><identifier>ISSN: 2052-1537</identifier><identifier>EISSN: 2052-1537</identifier><identifier>DOI: 10.1039/C7QM00198C</identifier><language>eng</language><ispartof>Materials chemistry frontiers, 2017-10, Vol.1 (10), p.2013-2026</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c272t-9753ff67b99a9db339720b9d77138b4c47e3c4dd161a4226a1ff580334557a183</citedby><cites>FETCH-LOGICAL-c272t-9753ff67b99a9db339720b9d77138b4c47e3c4dd161a4226a1ff580334557a183</cites><orcidid>0000-0001-9809-724X ; 0000-0002-0944-1115</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Denißen, Melanie</creatorcontrib><creatorcontrib>Nirmalananthan, Nithiya</creatorcontrib><creatorcontrib>Behnke, Thomas</creatorcontrib><creatorcontrib>Hoffmann, Katrin</creatorcontrib><creatorcontrib>Resch-Genger, Ute</creatorcontrib><creatorcontrib>Müller, Thomas J. J.</creatorcontrib><title>3-Piperazinyl propenylidene indolone merocyanines: consecutive three-component synthesis and electronic properties of solid-state luminophores with AIE properties</title><title>Materials chemistry frontiers</title><description>A series of twelve 3-piperazinyl propenylidene indolone merocyanines was synthesized in a one-pot fashion using a consecutive three-component insertion-coupling-Michael addition sequence. Physical-organic treatment of the absorption data of a consanguineous series of this library allows semiquantitative Linear Free Energy Relationships (LFERs) to be established and confirmation of the positive absorption solvatochromicity. All Boc-substituted piperazinyl merocyanines display aggregation induced emission (AIE), which was corroborated for two solvent systems. In particular, crystallization-induced emission enhancement (CIEE) induced by ultrasonication could be shown for a model chromophore by confocal laser scanning microscopy (CLSM).</description><issn>2052-1537</issn><issn>2052-1537</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNpNkM1KxDAUhYMoOIyz8QmyFqr5aZvG3VBGHRhRQdclTW9ppE1KklHq4_ikVkZwVveD-3EOHIQuKbmmhMubUrw8EkJlUZ6gBSMZS2jGxekRn6NVCO9kloRgnNAF-ubJsxnBqy9jpx6P3o0wg2nAAja2cb2bYQDv9KSssRBusXY2gN5H8wE4dh4g0W4YZ89GHCYbOwgmYGUbDD3o6J01-pDso4GAXYuDmyuSEFUE3O8HY93YOT__Pk3s8Hq7OfIv0Fmr-gCrv7tEb3eb1_Ih2T3db8v1LtFMsJhIkfG2zUUtpZJNzbkUjNSyEYLyok51KoDrtGloTlXKWK5o22YF4TzNMqFowZfo6pCrvQvBQ1uN3gzKTxUl1e_A1f_A_AdbenJo</recordid><startdate>20171001</startdate><enddate>20171001</enddate><creator>Denißen, Melanie</creator><creator>Nirmalananthan, Nithiya</creator><creator>Behnke, Thomas</creator><creator>Hoffmann, Katrin</creator><creator>Resch-Genger, Ute</creator><creator>Müller, Thomas J. J.</creator><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-9809-724X</orcidid><orcidid>https://orcid.org/0000-0002-0944-1115</orcidid></search><sort><creationdate>20171001</creationdate><title>3-Piperazinyl propenylidene indolone merocyanines: consecutive three-component synthesis and electronic properties of solid-state luminophores with AIE properties</title><author>Denißen, Melanie ; Nirmalananthan, Nithiya ; Behnke, Thomas ; Hoffmann, Katrin ; Resch-Genger, Ute ; Müller, Thomas J. J.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c272t-9753ff67b99a9db339720b9d77138b4c47e3c4dd161a4226a1ff580334557a183</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Denißen, Melanie</creatorcontrib><creatorcontrib>Nirmalananthan, Nithiya</creatorcontrib><creatorcontrib>Behnke, Thomas</creatorcontrib><creatorcontrib>Hoffmann, Katrin</creatorcontrib><creatorcontrib>Resch-Genger, Ute</creatorcontrib><creatorcontrib>Müller, Thomas J. J.</creatorcontrib><collection>CrossRef</collection><jtitle>Materials chemistry frontiers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Denißen, Melanie</au><au>Nirmalananthan, Nithiya</au><au>Behnke, Thomas</au><au>Hoffmann, Katrin</au><au>Resch-Genger, Ute</au><au>Müller, Thomas J. J.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>3-Piperazinyl propenylidene indolone merocyanines: consecutive three-component synthesis and electronic properties of solid-state luminophores with AIE properties</atitle><jtitle>Materials chemistry frontiers</jtitle><date>2017-10-01</date><risdate>2017</risdate><volume>1</volume><issue>10</issue><spage>2013</spage><epage>2026</epage><pages>2013-2026</pages><issn>2052-1537</issn><eissn>2052-1537</eissn><abstract>A series of twelve 3-piperazinyl propenylidene indolone merocyanines was synthesized in a one-pot fashion using a consecutive three-component insertion-coupling-Michael addition sequence. Physical-organic treatment of the absorption data of a consanguineous series of this library allows semiquantitative Linear Free Energy Relationships (LFERs) to be established and confirmation of the positive absorption solvatochromicity. All Boc-substituted piperazinyl merocyanines display aggregation induced emission (AIE), which was corroborated for two solvent systems. In particular, crystallization-induced emission enhancement (CIEE) induced by ultrasonication could be shown for a model chromophore by confocal laser scanning microscopy (CLSM).</abstract><doi>10.1039/C7QM00198C</doi><tpages>14</tpages><orcidid>https://orcid.org/0000-0001-9809-724X</orcidid><orcidid>https://orcid.org/0000-0002-0944-1115</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 2052-1537
ispartof Materials chemistry frontiers, 2017-10, Vol.1 (10), p.2013-2026
issn 2052-1537
2052-1537
language eng
recordid cdi_crossref_primary_10_1039_C7QM00198C
source Royal Society of Chemistry Journals
title 3-Piperazinyl propenylidene indolone merocyanines: consecutive three-component synthesis and electronic properties of solid-state luminophores with AIE properties
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-27T15%3A24%3A01IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-crossref&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=3-Piperazinyl%20propenylidene%20indolone%20merocyanines:%20consecutive%20three-component%20synthesis%20and%20electronic%20properties%20of%20solid-state%20luminophores%20with%20AIE%20properties&rft.jtitle=Materials%20chemistry%20frontiers&rft.au=Deni%C3%9Fen,%20Melanie&rft.date=2017-10-01&rft.volume=1&rft.issue=10&rft.spage=2013&rft.epage=2026&rft.pages=2013-2026&rft.issn=2052-1537&rft.eissn=2052-1537&rft_id=info:doi/10.1039/C7QM00198C&rft_dat=%3Ccrossref%3E10_1039_C7QM00198C%3C/crossref%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c272t-9753ff67b99a9db339720b9d77138b4c47e3c4dd161a4226a1ff580334557a183%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true