N,O π-Conjugated 4‑Substituted 1,3-Thiazole BF2 Complexes: Synthesis and Photophysical Properties

A series of 1,3-thiazole-based organoboron complexes has been designed and synthesized by acylation of 2-amino 4-subsituted 1,3-thiazoles with (4-dimethylamino)­benzoyl chloride and the subsequent BF2 complexation reaction. The influence of substituents in position 4 of the thiazole ring on photophy...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2018-02, Vol.83 (3), p.1095-1105
Main Authors: Potopnyk, Mykhaylo A, Lytvyn, Roman, Danyliv, Yan, Ceborska, Magdalena, Bezvikonnyi, Oleksandr, Volyniuk, Dmytro, Gražulevičius, Juozas Vidas
Format: Article
Language:English
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by
cites
container_end_page 1105
container_issue 3
container_start_page 1095
container_title Journal of organic chemistry
container_volume 83
creator Potopnyk, Mykhaylo A
Lytvyn, Roman
Danyliv, Yan
Ceborska, Magdalena
Bezvikonnyi, Oleksandr
Volyniuk, Dmytro
Gražulevičius, Juozas Vidas
description A series of 1,3-thiazole-based organoboron complexes has been designed and synthesized by acylation of 2-amino 4-subsituted 1,3-thiazoles with (4-dimethylamino)­benzoyl chloride and the subsequent BF2 complexation reaction. The influence of substituents in position 4 of the thiazole ring on photophysical properties of the complexes has been investigated. Synthesized thiazolo­[3,2-c]­[1,3,5,2]­oxadiazaborinines mainly showed intensive fluorescence in solutions. Complex with a 4,5-unsubstituted thiazole unit demonstrated an aggregation induced emission (AIE) effect and a very high fluorescent quantum yield (94%) in the solid state because of the inhibition of π–π/π–n interactions in the molecular packing.
doi_str_mv 10.1021/acs.joc.7b02239
format article
fullrecord <record><control><sourceid>proquest_acs_j</sourceid><recordid>TN_cdi_proquest_miscellaneous_1984751034</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1984751034</sourcerecordid><originalsourceid>FETCH-LOGICAL-a224t-8d7830730b650c32098f1a074b1a0e41f052a6b019f766626391ca7d8dd180c63</originalsourceid><addsrcrecordid>eNotkEFOwzAQRS0EEqWwZuslEk0Z24mdsIOIAlJFK7WsI8dxSKI0DrEjUVa9AifjDpyEVO0sZjRfX6M_D6FrAlMClNxJZaeVUVORAqUsOkEjElDweAT-KRrBIHqMcnaOLqytYKggCEYoe5ss8O_Oi01T9R_S6Qz7f7ufVZ9aV7p-v5MJ89ZFKb9NrfHjjOLYbNpaf2l7j1fbxhXalhbLJsPLwjjTFltbKlnjZWda3blS20t0lsva6qvjHKP32dM6fvHmi-fX-GHuSUp954WZCBkIBikPQDEKUZgTCcJPh659kkNAJU-BRLngnA_PRERJkYVZRkJQnI3RzeFu25nPXluXbEqrdF3LRpveJiQKfREQYP5gvT1YB2xJZfquGYIlBJI9y-QgquTIkv0DYvxodg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1984751034</pqid></control><display><type>article</type><title>N,O π-Conjugated 4‑Substituted 1,3-Thiazole BF2 Complexes: Synthesis and Photophysical Properties</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Potopnyk, Mykhaylo A ; Lytvyn, Roman ; Danyliv, Yan ; Ceborska, Magdalena ; Bezvikonnyi, Oleksandr ; Volyniuk, Dmytro ; Gražulevičius, Juozas Vidas</creator><creatorcontrib>Potopnyk, Mykhaylo A ; Lytvyn, Roman ; Danyliv, Yan ; Ceborska, Magdalena ; Bezvikonnyi, Oleksandr ; Volyniuk, Dmytro ; Gražulevičius, Juozas Vidas</creatorcontrib><description>A series of 1,3-thiazole-based organoboron complexes has been designed and synthesized by acylation of 2-amino 4-subsituted 1,3-thiazoles with (4-dimethylamino)­benzoyl chloride and the subsequent BF2 complexation reaction. The influence of substituents in position 4 of the thiazole ring on photophysical properties of the complexes has been investigated. Synthesized thiazolo­[3,2-c]­[1,3,5,2]­oxadiazaborinines mainly showed intensive fluorescence in solutions. Complex with a 4,5-unsubstituted thiazole unit demonstrated an aggregation induced emission (AIE) effect and a very high fluorescent quantum yield (94%) in the solid state because of the inhibition of π–π/π–n interactions in the molecular packing.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.7b02239</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2018-02, Vol.83 (3), p.1095-1105</ispartof><rights>Copyright © 2018 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0001-9645-0337 ; 0000-0002-4543-2785</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Potopnyk, Mykhaylo A</creatorcontrib><creatorcontrib>Lytvyn, Roman</creatorcontrib><creatorcontrib>Danyliv, Yan</creatorcontrib><creatorcontrib>Ceborska, Magdalena</creatorcontrib><creatorcontrib>Bezvikonnyi, Oleksandr</creatorcontrib><creatorcontrib>Volyniuk, Dmytro</creatorcontrib><creatorcontrib>Gražulevičius, Juozas Vidas</creatorcontrib><title>N,O π-Conjugated 4‑Substituted 1,3-Thiazole BF2 Complexes: Synthesis and Photophysical Properties</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A series of 1,3-thiazole-based organoboron complexes has been designed and synthesized by acylation of 2-amino 4-subsituted 1,3-thiazoles with (4-dimethylamino)­benzoyl chloride and the subsequent BF2 complexation reaction. The influence of substituents in position 4 of the thiazole ring on photophysical properties of the complexes has been investigated. Synthesized thiazolo­[3,2-c]­[1,3,5,2]­oxadiazaborinines mainly showed intensive fluorescence in solutions. Complex with a 4,5-unsubstituted thiazole unit demonstrated an aggregation induced emission (AIE) effect and a very high fluorescent quantum yield (94%) in the solid state because of the inhibition of π–π/π–n interactions in the molecular packing.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNotkEFOwzAQRS0EEqWwZuslEk0Z24mdsIOIAlJFK7WsI8dxSKI0DrEjUVa9AifjDpyEVO0sZjRfX6M_D6FrAlMClNxJZaeVUVORAqUsOkEjElDweAT-KRrBIHqMcnaOLqytYKggCEYoe5ss8O_Oi01T9R_S6Qz7f7ufVZ9aV7p-v5MJ89ZFKb9NrfHjjOLYbNpaf2l7j1fbxhXalhbLJsPLwjjTFltbKlnjZWda3blS20t0lsva6qvjHKP32dM6fvHmi-fX-GHuSUp954WZCBkIBikPQDEKUZgTCcJPh659kkNAJU-BRLngnA_PRERJkYVZRkJQnI3RzeFu25nPXluXbEqrdF3LRpveJiQKfREQYP5gvT1YB2xJZfquGYIlBJI9y-QgquTIkv0DYvxodg</recordid><startdate>20180202</startdate><enddate>20180202</enddate><creator>Potopnyk, Mykhaylo A</creator><creator>Lytvyn, Roman</creator><creator>Danyliv, Yan</creator><creator>Ceborska, Magdalena</creator><creator>Bezvikonnyi, Oleksandr</creator><creator>Volyniuk, Dmytro</creator><creator>Gražulevičius, Juozas Vidas</creator><general>American Chemical Society</general><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-9645-0337</orcidid><orcidid>https://orcid.org/0000-0002-4543-2785</orcidid></search><sort><creationdate>20180202</creationdate><title>N,O π-Conjugated 4‑Substituted 1,3-Thiazole BF2 Complexes: Synthesis and Photophysical Properties</title><author>Potopnyk, Mykhaylo A ; Lytvyn, Roman ; Danyliv, Yan ; Ceborska, Magdalena ; Bezvikonnyi, Oleksandr ; Volyniuk, Dmytro ; Gražulevičius, Juozas Vidas</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a224t-8d7830730b650c32098f1a074b1a0e41f052a6b019f766626391ca7d8dd180c63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Potopnyk, Mykhaylo A</creatorcontrib><creatorcontrib>Lytvyn, Roman</creatorcontrib><creatorcontrib>Danyliv, Yan</creatorcontrib><creatorcontrib>Ceborska, Magdalena</creatorcontrib><creatorcontrib>Bezvikonnyi, Oleksandr</creatorcontrib><creatorcontrib>Volyniuk, Dmytro</creatorcontrib><creatorcontrib>Gražulevičius, Juozas Vidas</creatorcontrib><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Potopnyk, Mykhaylo A</au><au>Lytvyn, Roman</au><au>Danyliv, Yan</au><au>Ceborska, Magdalena</au><au>Bezvikonnyi, Oleksandr</au><au>Volyniuk, Dmytro</au><au>Gražulevičius, Juozas Vidas</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>N,O π-Conjugated 4‑Substituted 1,3-Thiazole BF2 Complexes: Synthesis and Photophysical Properties</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2018-02-02</date><risdate>2018</risdate><volume>83</volume><issue>3</issue><spage>1095</spage><epage>1105</epage><pages>1095-1105</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>A series of 1,3-thiazole-based organoboron complexes has been designed and synthesized by acylation of 2-amino 4-subsituted 1,3-thiazoles with (4-dimethylamino)­benzoyl chloride and the subsequent BF2 complexation reaction. The influence of substituents in position 4 of the thiazole ring on photophysical properties of the complexes has been investigated. Synthesized thiazolo­[3,2-c]­[1,3,5,2]­oxadiazaborinines mainly showed intensive fluorescence in solutions. Complex with a 4,5-unsubstituted thiazole unit demonstrated an aggregation induced emission (AIE) effect and a very high fluorescent quantum yield (94%) in the solid state because of the inhibition of π–π/π–n interactions in the molecular packing.</abstract><pub>American Chemical Society</pub><doi>10.1021/acs.joc.7b02239</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0001-9645-0337</orcidid><orcidid>https://orcid.org/0000-0002-4543-2785</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2018-02, Vol.83 (3), p.1095-1105
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_1984751034
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title N,O π-Conjugated 4‑Substituted 1,3-Thiazole BF2 Complexes: Synthesis and Photophysical Properties
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-29T13%3A16%3A28IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_acs_j&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=N,O%20%CF%80-Conjugated%204%E2%80%91Substituted%201,3-Thiazole%20BF2%20Complexes:%20Synthesis%20and%20Photophysical%20Properties&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Potopnyk,%20Mykhaylo%20A&rft.date=2018-02-02&rft.volume=83&rft.issue=3&rft.spage=1095&rft.epage=1105&rft.pages=1095-1105&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.7b02239&rft_dat=%3Cproquest_acs_j%3E1984751034%3C/proquest_acs_j%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a224t-8d7830730b650c32098f1a074b1a0e41f052a6b019f766626391ca7d8dd180c63%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1984751034&rft_id=info:pmid/&rfr_iscdi=true