Effective targeting of proton transfer at ground and excited states of ortho-(2'-imidazolyl)naphthol constitutional isomers
Steady-state and time-resolved spectroscopy and quantum chemical computational studies were employed to investigate ground and excited state proton transfer of a novel series of ortho-(1H-imidazol-2-yl)naphthol constitutional isomers: 1-(1H-imidazol-2-yl)naphthalen-2-ol (1NI2OH), 2-(1H-imidazol-2-yl...
Gespeichert in:
| Veröffentlicht in: | Physical chemistry chemical physics : PCCP 2015-01, Vol.17 (4), p.2404-2415 |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 2415 |
|---|---|
| container_issue | 4 |
| container_start_page | 2404 |
| container_title | Physical chemistry chemical physics : PCCP |
| container_volume | 17 |
| creator | Oliveira, Thaís C F Carmo, Luiz F V Murta, Bárbara Duarte, Luís G T A Nome, Rene A Rocha, Willian R Brandão, Tiago A S |
| description | Steady-state and time-resolved spectroscopy and quantum chemical computational studies were employed to investigate ground and excited state proton transfer of a novel series of ortho-(1H-imidazol-2-yl)naphthol constitutional isomers: 1-(1H-imidazol-2-yl)naphthalen-2-ol (1NI2OH), 2-(1H-imidazol-2-yl)naphthalen-1-ol (2NI1OH) and 3-(1H-imidazol-2-yl)naphthalen-2-ol (3NI2OH). Proper Near Attack Conformations (NACs) involving a strong intramolecular hydrogen bond between the naphthol moiety and the ortho-imidazole group account for the highest ground state acidity of 2NI1OH compared with 1NI2OH and 3NI2OH. Moreover, ESIPT for 2NI1OH and 3NI2OH is further associated with planar chelate H-ring formation whereas 1NI2OH shows the highest ESIPT barrier and a noncoplanar imidazole group. In addition to energetic and structural requirements, the final state also depends on electronic configuration of the ESIPT product with the neutral 3NI2OH showing an ICT effect that correlates with the excited state pKa of the cationic species. |
| doi_str_mv | 10.1039/c4cp04337e |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1651416921</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1640480480</sourcerecordid><originalsourceid>FETCH-LOGICAL-c320t-a5d56f00e78aeaba863d516385c2f4a7b6873ab6e4cc508a290781fa5f140ece3</originalsourceid><addsrcrecordid>eNqNkVtLxDAQhYMo3l_8AZI3V6GaNJd2H2VZLyDogz6X2XSyRtpmTVLx8uftuqvPwgxzGD4OHA4hR5ydcybGF0aaBZNCFLhBdrnUIhuzUm7-6ULvkL0YXxhjXHGxTXZyJcdM8nyXfE2tRZPcG9IEYY7JdXPqLV0En3xHU4AuWgwUEp0H33c1hWHx3biENY0JEsYl70N69tkoP8lc62r49M1Hc9rB4nl4N9T4LiaX-uR8Bw110bcY4gHZstBEPFzfffJ0NX2c3GR399e3k8u7zIicpQxUrbRlDIsSEGZQalErrkWpTG4lFDNdFgJmGqUxipWQD4lLbkFZLhkaFPtktPIdQr32GFPVumiwaaBD38eKa8Ul1-Oc_wOVTJbLGdCzFWqCjzGgrRbBtRA-Ks6qZS_VRE4efnqZDvDx2reftVj_ob9FiG_unYo3</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1640480480</pqid></control><display><type>article</type><title>Effective targeting of proton transfer at ground and excited states of ortho-(2'-imidazolyl)naphthol constitutional isomers</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Oliveira, Thaís C F ; Carmo, Luiz F V ; Murta, Bárbara ; Duarte, Luís G T A ; Nome, Rene A ; Rocha, Willian R ; Brandão, Tiago A S</creator><creatorcontrib>Oliveira, Thaís C F ; Carmo, Luiz F V ; Murta, Bárbara ; Duarte, Luís G T A ; Nome, Rene A ; Rocha, Willian R ; Brandão, Tiago A S</creatorcontrib><description>Steady-state and time-resolved spectroscopy and quantum chemical computational studies were employed to investigate ground and excited state proton transfer of a novel series of ortho-(1H-imidazol-2-yl)naphthol constitutional isomers: 1-(1H-imidazol-2-yl)naphthalen-2-ol (1NI2OH), 2-(1H-imidazol-2-yl)naphthalen-1-ol (2NI1OH) and 3-(1H-imidazol-2-yl)naphthalen-2-ol (3NI2OH). Proper Near Attack Conformations (NACs) involving a strong intramolecular hydrogen bond between the naphthol moiety and the ortho-imidazole group account for the highest ground state acidity of 2NI1OH compared with 1NI2OH and 3NI2OH. Moreover, ESIPT for 2NI1OH and 3NI2OH is further associated with planar chelate H-ring formation whereas 1NI2OH shows the highest ESIPT barrier and a noncoplanar imidazole group. In addition to energetic and structural requirements, the final state also depends on electronic configuration of the ESIPT product with the neutral 3NI2OH showing an ICT effect that correlates with the excited state pKa of the cationic species.</description><identifier>ISSN: 1463-9076</identifier><identifier>EISSN: 1463-9084</identifier><identifier>DOI: 10.1039/c4cp04337e</identifier><identifier>PMID: 25490412</identifier><language>eng</language><publisher>England</publisher><subject>Cationic ; Electronics ; Excitation ; Ground state ; Grounds ; Imidazole ; Isomers ; Quantum chemistry</subject><ispartof>Physical chemistry chemical physics : PCCP, 2015-01, Vol.17 (4), p.2404-2415</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c320t-a5d56f00e78aeaba863d516385c2f4a7b6873ab6e4cc508a290781fa5f140ece3</citedby><cites>FETCH-LOGICAL-c320t-a5d56f00e78aeaba863d516385c2f4a7b6873ab6e4cc508a290781fa5f140ece3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785,27929,27930</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25490412$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Oliveira, Thaís C F</creatorcontrib><creatorcontrib>Carmo, Luiz F V</creatorcontrib><creatorcontrib>Murta, Bárbara</creatorcontrib><creatorcontrib>Duarte, Luís G T A</creatorcontrib><creatorcontrib>Nome, Rene A</creatorcontrib><creatorcontrib>Rocha, Willian R</creatorcontrib><creatorcontrib>Brandão, Tiago A S</creatorcontrib><title>Effective targeting of proton transfer at ground and excited states of ortho-(2'-imidazolyl)naphthol constitutional isomers</title><title>Physical chemistry chemical physics : PCCP</title><addtitle>Phys Chem Chem Phys</addtitle><description>Steady-state and time-resolved spectroscopy and quantum chemical computational studies were employed to investigate ground and excited state proton transfer of a novel series of ortho-(1H-imidazol-2-yl)naphthol constitutional isomers: 1-(1H-imidazol-2-yl)naphthalen-2-ol (1NI2OH), 2-(1H-imidazol-2-yl)naphthalen-1-ol (2NI1OH) and 3-(1H-imidazol-2-yl)naphthalen-2-ol (3NI2OH). Proper Near Attack Conformations (NACs) involving a strong intramolecular hydrogen bond between the naphthol moiety and the ortho-imidazole group account for the highest ground state acidity of 2NI1OH compared with 1NI2OH and 3NI2OH. Moreover, ESIPT for 2NI1OH and 3NI2OH is further associated with planar chelate H-ring formation whereas 1NI2OH shows the highest ESIPT barrier and a noncoplanar imidazole group. In addition to energetic and structural requirements, the final state also depends on electronic configuration of the ESIPT product with the neutral 3NI2OH showing an ICT effect that correlates with the excited state pKa of the cationic species.</description><subject>Cationic</subject><subject>Electronics</subject><subject>Excitation</subject><subject>Ground state</subject><subject>Grounds</subject><subject>Imidazole</subject><subject>Isomers</subject><subject>Quantum chemistry</subject><issn>1463-9076</issn><issn>1463-9084</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqNkVtLxDAQhYMo3l_8AZI3V6GaNJd2H2VZLyDogz6X2XSyRtpmTVLx8uftuqvPwgxzGD4OHA4hR5ydcybGF0aaBZNCFLhBdrnUIhuzUm7-6ULvkL0YXxhjXHGxTXZyJcdM8nyXfE2tRZPcG9IEYY7JdXPqLV0En3xHU4AuWgwUEp0H33c1hWHx3biENY0JEsYl70N69tkoP8lc62r49M1Hc9rB4nl4N9T4LiaX-uR8Bw110bcY4gHZstBEPFzfffJ0NX2c3GR399e3k8u7zIicpQxUrbRlDIsSEGZQalErrkWpTG4lFDNdFgJmGqUxipWQD4lLbkFZLhkaFPtktPIdQr32GFPVumiwaaBD38eKa8Ul1-Oc_wOVTJbLGdCzFWqCjzGgrRbBtRA-Ks6qZS_VRE4efnqZDvDx2reftVj_ob9FiG_unYo3</recordid><startdate>20150128</startdate><enddate>20150128</enddate><creator>Oliveira, Thaís C F</creator><creator>Carmo, Luiz F V</creator><creator>Murta, Bárbara</creator><creator>Duarte, Luís G T A</creator><creator>Nome, Rene A</creator><creator>Rocha, Willian R</creator><creator>Brandão, Tiago A S</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20150128</creationdate><title>Effective targeting of proton transfer at ground and excited states of ortho-(2'-imidazolyl)naphthol constitutional isomers</title><author>Oliveira, Thaís C F ; Carmo, Luiz F V ; Murta, Bárbara ; Duarte, Luís G T A ; Nome, Rene A ; Rocha, Willian R ; Brandão, Tiago A S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c320t-a5d56f00e78aeaba863d516385c2f4a7b6873ab6e4cc508a290781fa5f140ece3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Cationic</topic><topic>Electronics</topic><topic>Excitation</topic><topic>Ground state</topic><topic>Grounds</topic><topic>Imidazole</topic><topic>Isomers</topic><topic>Quantum chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Oliveira, Thaís C F</creatorcontrib><creatorcontrib>Carmo, Luiz F V</creatorcontrib><creatorcontrib>Murta, Bárbara</creatorcontrib><creatorcontrib>Duarte, Luís G T A</creatorcontrib><creatorcontrib>Nome, Rene A</creatorcontrib><creatorcontrib>Rocha, Willian R</creatorcontrib><creatorcontrib>Brandão, Tiago A S</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Physical chemistry chemical physics : PCCP</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Oliveira, Thaís C F</au><au>Carmo, Luiz F V</au><au>Murta, Bárbara</au><au>Duarte, Luís G T A</au><au>Nome, Rene A</au><au>Rocha, Willian R</au><au>Brandão, Tiago A S</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Effective targeting of proton transfer at ground and excited states of ortho-(2'-imidazolyl)naphthol constitutional isomers</atitle><jtitle>Physical chemistry chemical physics : PCCP</jtitle><addtitle>Phys Chem Chem Phys</addtitle><date>2015-01-28</date><risdate>2015</risdate><volume>17</volume><issue>4</issue><spage>2404</spage><epage>2415</epage><pages>2404-2415</pages><issn>1463-9076</issn><eissn>1463-9084</eissn><abstract>Steady-state and time-resolved spectroscopy and quantum chemical computational studies were employed to investigate ground and excited state proton transfer of a novel series of ortho-(1H-imidazol-2-yl)naphthol constitutional isomers: 1-(1H-imidazol-2-yl)naphthalen-2-ol (1NI2OH), 2-(1H-imidazol-2-yl)naphthalen-1-ol (2NI1OH) and 3-(1H-imidazol-2-yl)naphthalen-2-ol (3NI2OH). Proper Near Attack Conformations (NACs) involving a strong intramolecular hydrogen bond between the naphthol moiety and the ortho-imidazole group account for the highest ground state acidity of 2NI1OH compared with 1NI2OH and 3NI2OH. Moreover, ESIPT for 2NI1OH and 3NI2OH is further associated with planar chelate H-ring formation whereas 1NI2OH shows the highest ESIPT barrier and a noncoplanar imidazole group. In addition to energetic and structural requirements, the final state also depends on electronic configuration of the ESIPT product with the neutral 3NI2OH showing an ICT effect that correlates with the excited state pKa of the cationic species.</abstract><cop>England</cop><pmid>25490412</pmid><doi>10.1039/c4cp04337e</doi><tpages>12</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1463-9076 |
| ispartof | Physical chemistry chemical physics : PCCP, 2015-01, Vol.17 (4), p.2404-2415 |
| issn | 1463-9076 1463-9084 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1651416921 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Cationic Electronics Excitation Ground state Grounds Imidazole Isomers Quantum chemistry |
| title | Effective targeting of proton transfer at ground and excited states of ortho-(2'-imidazolyl)naphthol constitutional isomers |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-14T06%3A50%3A43IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Effective%20targeting%20of%20proton%20transfer%20at%20ground%20and%20excited%20states%20of%20ortho-(2'-imidazolyl)naphthol%20constitutional%20isomers&rft.jtitle=Physical%20chemistry%20chemical%20physics%20:%20PCCP&rft.au=Oliveira,%20Tha%C3%ADs%20C%20F&rft.date=2015-01-28&rft.volume=17&rft.issue=4&rft.spage=2404&rft.epage=2415&rft.pages=2404-2415&rft.issn=1463-9076&rft.eissn=1463-9084&rft_id=info:doi/10.1039/c4cp04337e&rft_dat=%3Cproquest_cross%3E1640480480%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1640480480&rft_id=info:pmid/25490412&rfr_iscdi=true |