Anion Recognition by a Pincer-Type Host Constructed from Two Polyamide Macrocyclic Frameworks Jointed by a Photo-Addressable Azobenzene Switch
A sterically crowded light-responsive host was synthetized with a 93% yield by applying a post-functionalization protocol utilizing the double amidation of 4,4'-azodibenzoyl dichloride with a readily available 26-membered macrocyclic amine. X-ray structures of two hydrates of - demonstrate a ve...
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| Veröffentlicht in: | Materials 2022-01, Vol.15 (2), p.692 |
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| creator | Niedbała, Patryk Ceborska, Magdalena Mehmet, Mart Ignacak, Wiktor Jurczak, Janusz Dąbrowa, Kajetan |
| description | A sterically crowded light-responsive host
was synthetized with a 93% yield by applying a post-functionalization protocol utilizing the double amidation of 4,4'-azodibenzoyl dichloride with a readily available 26-membered macrocyclic amine. X-ray structures of two hydrates of
-
demonstrate a very different alignment of the azobenzene linkage, which is involved in
-shape or parallel-displaced π⋯π stacking interactions with the pyridine-2,6-dicarboxamide moieties from the macrocyclic backbone. Despite the rigidity of the macrocyclic framework, which generates a large steric hindrance around the azobenzene chromophore, the host
retains the ability to undergo a reversible
⟷
isomerization upon irradiation with UVA (368 nm) and blue (410 nm) light. Moreover, thermal
→
back-isomerization (ΔG
= 106.5 kJ∙mol
,
= 141 h) is markedly slowed down as compared to the non-macrocyclic analog.
H NMR titration experiments in DMSO-
/0.5% water solution reveal that
-
exhibits a strong preference for dihydrogenphosphate (H
PO
) over other anions (Cl
, MeCO
, and PhCO
), whereas the photogenerated metastable
-
shows lower affinity for the H
PO
anion. |
| doi_str_mv | 10.3390/ma15020692 |
| format | Article |
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was synthetized with a 93% yield by applying a post-functionalization protocol utilizing the double amidation of 4,4'-azodibenzoyl dichloride with a readily available 26-membered macrocyclic amine. X-ray structures of two hydrates of
-
demonstrate a very different alignment of the azobenzene linkage, which is involved in
-shape or parallel-displaced π⋯π stacking interactions with the pyridine-2,6-dicarboxamide moieties from the macrocyclic backbone. Despite the rigidity of the macrocyclic framework, which generates a large steric hindrance around the azobenzene chromophore, the host
retains the ability to undergo a reversible
⟷
isomerization upon irradiation with UVA (368 nm) and blue (410 nm) light. Moreover, thermal
→
back-isomerization (ΔG
= 106.5 kJ∙mol
,
= 141 h) is markedly slowed down as compared to the non-macrocyclic analog.
H NMR titration experiments in DMSO-
/0.5% water solution reveal that
-
exhibits a strong preference for dihydrogenphosphate (H
PO
) over other anions (Cl
, MeCO
, and PhCO
), whereas the photogenerated metastable
-
shows lower affinity for the H
PO
anion.</description><identifier>ISSN: 1996-1944</identifier><identifier>EISSN: 1996-1944</identifier><identifier>DOI: 10.3390/ma15020692</identifier><identifier>PMID: 35057408</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Anions ; Azo compounds ; Chromophores ; Dichlorides ; Hydrates ; Hydrogen bonds ; Isomerization ; NMR ; Nuclear magnetic resonance ; Polyamide resins ; Single crystals ; Software packages ; Steric hindrance ; Titration</subject><ispartof>Materials, 2022-01, Vol.15 (2), p.692</ispartof><rights>2022 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2022 by the authors. 2022</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c406t-deba010d87a470c8d41a7aa8684d5e40624fe35c7adf6d0f32a28c04d24241c13</citedby><cites>FETCH-LOGICAL-c406t-deba010d87a470c8d41a7aa8684d5e40624fe35c7adf6d0f32a28c04d24241c13</cites><orcidid>0000-0002-0351-6614 ; 0000-0001-7767-5303 ; 0000-0003-1452-7332</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/PMC8777895/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8777895/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,27924,27925,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35057408$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Niedbała, Patryk</creatorcontrib><creatorcontrib>Ceborska, Magdalena</creatorcontrib><creatorcontrib>Mehmet, Mart</creatorcontrib><creatorcontrib>Ignacak, Wiktor</creatorcontrib><creatorcontrib>Jurczak, Janusz</creatorcontrib><creatorcontrib>Dąbrowa, Kajetan</creatorcontrib><title>Anion Recognition by a Pincer-Type Host Constructed from Two Polyamide Macrocyclic Frameworks Jointed by a Photo-Addressable Azobenzene Switch</title><title>Materials</title><addtitle>Materials (Basel)</addtitle><description>A sterically crowded light-responsive host
was synthetized with a 93% yield by applying a post-functionalization protocol utilizing the double amidation of 4,4'-azodibenzoyl dichloride with a readily available 26-membered macrocyclic amine. X-ray structures of two hydrates of
-
demonstrate a very different alignment of the azobenzene linkage, which is involved in
-shape or parallel-displaced π⋯π stacking interactions with the pyridine-2,6-dicarboxamide moieties from the macrocyclic backbone. Despite the rigidity of the macrocyclic framework, which generates a large steric hindrance around the azobenzene chromophore, the host
retains the ability to undergo a reversible
⟷
isomerization upon irradiation with UVA (368 nm) and blue (410 nm) light. Moreover, thermal
→
back-isomerization (ΔG
= 106.5 kJ∙mol
,
= 141 h) is markedly slowed down as compared to the non-macrocyclic analog.
H NMR titration experiments in DMSO-
/0.5% water solution reveal that
-
exhibits a strong preference for dihydrogenphosphate (H
PO
) over other anions (Cl
, MeCO
, and PhCO
), whereas the photogenerated metastable
-
shows lower affinity for the H
PO
anion.</description><subject>Anions</subject><subject>Azo compounds</subject><subject>Chromophores</subject><subject>Dichlorides</subject><subject>Hydrates</subject><subject>Hydrogen bonds</subject><subject>Isomerization</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Polyamide resins</subject><subject>Single crystals</subject><subject>Software packages</subject><subject>Steric hindrance</subject><subject>Titration</subject><issn>1996-1944</issn><issn>1996-1944</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><recordid>eNpdkc1u1DAUhS0EolXphgdAltggpID_EjsbpNGIUlARFQxry7FvOi6JPbUTRulD8MwkmlIK3vhI9_PRuT4IPafkDec1edsbWhJGqpo9Qse0rquC1kI8fqCP0GnO12Q-nFPF6qfoiJeklIKoY_RrFXwM-CvYeBX8sOhmwgZf-mAhFZtpB_g85gGvY8hDGu0ADrcp9nizj_gydpPpvQP82dgU7WQ7b_FZMj3sY_qR8afow_Li4LmNQyxWziXI2TQd4NVtbCDcQgD8be8Hu32GnrSmy3B6d5-g72fvN-vz4uLLh4_r1UVhBamGwkFjCCVOSSMkscoJaqQxqlLClTAjTLTASyuNaytHWs4MU5YIxwQT1FJ-gt4dfHdj04OzEIZkOr1Lvjdp0tF4_e8k-K2-ij-1klKqupwNXt0ZpHgzQh5077OFrjMB4pg1qxhjSs6BZvTlf-h1HFOY11soyoUsxUK9PlDzP-acoL0PQ4lemtZ_m57hFw_j36N_euW_AVCkpbs</recordid><startdate>20220117</startdate><enddate>20220117</enddate><creator>Niedbała, Patryk</creator><creator>Ceborska, Magdalena</creator><creator>Mehmet, Mart</creator><creator>Ignacak, Wiktor</creator><creator>Jurczak, Janusz</creator><creator>Dąbrowa, Kajetan</creator><general>MDPI AG</general><general>MDPI</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>D1I</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>KB.</scope><scope>PDBOC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-0351-6614</orcidid><orcidid>https://orcid.org/0000-0001-7767-5303</orcidid><orcidid>https://orcid.org/0000-0003-1452-7332</orcidid></search><sort><creationdate>20220117</creationdate><title>Anion Recognition by a Pincer-Type Host Constructed from Two Polyamide Macrocyclic Frameworks Jointed by a Photo-Addressable Azobenzene Switch</title><author>Niedbała, Patryk ; Ceborska, Magdalena ; Mehmet, Mart ; Ignacak, Wiktor ; Jurczak, Janusz ; Dąbrowa, Kajetan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c406t-deba010d87a470c8d41a7aa8684d5e40624fe35c7adf6d0f32a28c04d24241c13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Anions</topic><topic>Azo compounds</topic><topic>Chromophores</topic><topic>Dichlorides</topic><topic>Hydrates</topic><topic>Hydrogen bonds</topic><topic>Isomerization</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Polyamide resins</topic><topic>Single crystals</topic><topic>Software packages</topic><topic>Steric hindrance</topic><topic>Titration</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Niedbała, Patryk</creatorcontrib><creatorcontrib>Ceborska, Magdalena</creatorcontrib><creatorcontrib>Mehmet, Mart</creatorcontrib><creatorcontrib>Ignacak, Wiktor</creatorcontrib><creatorcontrib>Jurczak, Janusz</creatorcontrib><creatorcontrib>Dąbrowa, Kajetan</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Materials Science Collection</collection><collection>ProQuest Central Korea</collection><collection>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>Materials Science Database</collection><collection>Materials Science Collection</collection><collection>Access via ProQuest (Open Access)</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Materials</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Niedbała, Patryk</au><au>Ceborska, Magdalena</au><au>Mehmet, Mart</au><au>Ignacak, Wiktor</au><au>Jurczak, Janusz</au><au>Dąbrowa, Kajetan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Anion Recognition by a Pincer-Type Host Constructed from Two Polyamide Macrocyclic Frameworks Jointed by a Photo-Addressable Azobenzene Switch</atitle><jtitle>Materials</jtitle><addtitle>Materials (Basel)</addtitle><date>2022-01-17</date><risdate>2022</risdate><volume>15</volume><issue>2</issue><spage>692</spage><pages>692-</pages><issn>1996-1944</issn><eissn>1996-1944</eissn><abstract>A sterically crowded light-responsive host
was synthetized with a 93% yield by applying a post-functionalization protocol utilizing the double amidation of 4,4'-azodibenzoyl dichloride with a readily available 26-membered macrocyclic amine. X-ray structures of two hydrates of
-
demonstrate a very different alignment of the azobenzene linkage, which is involved in
-shape or parallel-displaced π⋯π stacking interactions with the pyridine-2,6-dicarboxamide moieties from the macrocyclic backbone. Despite the rigidity of the macrocyclic framework, which generates a large steric hindrance around the azobenzene chromophore, the host
retains the ability to undergo a reversible
⟷
isomerization upon irradiation with UVA (368 nm) and blue (410 nm) light. Moreover, thermal
→
back-isomerization (ΔG
= 106.5 kJ∙mol
,
= 141 h) is markedly slowed down as compared to the non-macrocyclic analog.
H NMR titration experiments in DMSO-
/0.5% water solution reveal that
-
exhibits a strong preference for dihydrogenphosphate (H
PO
) over other anions (Cl
, MeCO
, and PhCO
), whereas the photogenerated metastable
-
shows lower affinity for the H
PO
anion.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>35057408</pmid><doi>10.3390/ma15020692</doi><orcidid>https://orcid.org/0000-0002-0351-6614</orcidid><orcidid>https://orcid.org/0000-0001-7767-5303</orcidid><orcidid>https://orcid.org/0000-0003-1452-7332</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1996-1944 |
| ispartof | Materials, 2022-01, Vol.15 (2), p.692 |
| issn | 1996-1944 1996-1944 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_8777895 |
| source | PubMed Central Open Access; MDPI - Multidisciplinary Digital Publishing Institute; EZB-FREE-00999 freely available EZB journals; PubMed Central; Free Full-Text Journals in Chemistry |
| subjects | Anions Azo compounds Chromophores Dichlorides Hydrates Hydrogen bonds Isomerization NMR Nuclear magnetic resonance Polyamide resins Single crystals Software packages Steric hindrance Titration |
| title | Anion Recognition by a Pincer-Type Host Constructed from Two Polyamide Macrocyclic Frameworks Jointed by a Photo-Addressable Azobenzene Switch |
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