Synthesis, spectroscopic, and structural studies of extremely short chain basket handle porphyrins and their zinc(II) complexes
The synthesis of extremely short chain basket handle porphyrins is described. These molecules are derived from 5,10,15,20-tetraphenyl-21H,23H-porphine bearing alkoxy chains (handles) of 4-, 5-, and 6-carbon atoms covalently attached at the o-phenyl positions. For the n = 5 and 6 free base porphyrins...
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| Veröffentlicht in: | J. Am. Chem. Soc.; (United States) 1987-04, Vol.109 (9), p.2659-2668 |
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| container_title | J. Am. Chem. Soc.; (United States) |
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| creator | Simonis, Ursula Walker, F. Ann Lee, Patricia Lani Hanquet, Bernard J Meyerhoff, Dieter J Scheidt, W. Robert |
| description | The synthesis of extremely short chain basket handle porphyrins is described. These molecules are derived from 5,10,15,20-tetraphenyl-21H,23H-porphine bearing alkoxy chains (handles) of 4-, 5-, and 6-carbon atoms covalently attached at the o-phenyl positions. For the n = 5 and 6 free base porphyrins three different isomers are formed: cross-trans-linked (I), adjacent-trans-linked (II) and adjacent-cis-linked (III) isomers. For the butyl-bridged compound only the latter two could be obtained. Attempts to insert zinc(II) ion into the porphinato cores have been successful only for isomers II and III; isomer I could not be metalated. The structural assignment of the three different isomers is based on UV-vis and /sup 1/H NMR spectroscopy as well as on X-ray structure analysis of the Zn(II) complex of the hexyl-bridged isomer II. The Zn hexyl II complex crystallizes in the monoclinic system, space group P2/sub 1//n, and cell dimensions at 296 K of a = 8.608 (2) A, b = 22.212 (4) A, c = 13.774 (2) A, and ..beta.. = 91.90 (1)/sup 0/ with two molecules per unit cell. The average Zn-N bond distance is 2.031 (3) A with the zinc atom precisely centered in the porphinato plane. On the basis of the spectroscopic and preliminary structural data, it is shown that the porphyrin ring of isomer I is permanently distorted from planarity. Furthermore, from analysis of spectroscopic data for isomers II and III it appears likely that the porphyrin rings of the butyl-bridged compounds are also distorted significantly, while those of the pentyl- and hexyl-bridged porphyrins are planar. |
| doi_str_mv | 10.1021/ja00243a018 |
| format | Article |
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Ann ; Lee, Patricia Lani ; Hanquet, Bernard J ; Meyerhoff, Dieter J ; Scheidt, W. Robert</creator><creatorcontrib>Simonis, Ursula ; Walker, F. Ann ; Lee, Patricia Lani ; Hanquet, Bernard J ; Meyerhoff, Dieter J ; Scheidt, W. Robert ; San Francisco State Univ., CA</creatorcontrib><description>The synthesis of extremely short chain basket handle porphyrins is described. These molecules are derived from 5,10,15,20-tetraphenyl-21H,23H-porphine bearing alkoxy chains (handles) of 4-, 5-, and 6-carbon atoms covalently attached at the o-phenyl positions. For the n = 5 and 6 free base porphyrins three different isomers are formed: cross-trans-linked (I), adjacent-trans-linked (II) and adjacent-cis-linked (III) isomers. For the butyl-bridged compound only the latter two could be obtained. Attempts to insert zinc(II) ion into the porphinato cores have been successful only for isomers II and III; isomer I could not be metalated. The structural assignment of the three different isomers is based on UV-vis and /sup 1/H NMR spectroscopy as well as on X-ray structure analysis of the Zn(II) complex of the hexyl-bridged isomer II. The Zn hexyl II complex crystallizes in the monoclinic system, space group P2/sub 1//n, and cell dimensions at 296 K of a = 8.608 (2) A, b = 22.212 (4) A, c = 13.774 (2) A, and ..beta.. = 91.90 (1)/sup 0/ with two molecules per unit cell. The average Zn-N bond distance is 2.031 (3) A with the zinc atom precisely centered in the porphinato plane. On the basis of the spectroscopic and preliminary structural data, it is shown that the porphyrin ring of isomer I is permanently distorted from planarity. Furthermore, from analysis of spectroscopic data for isomers II and III it appears likely that the porphyrin rings of the butyl-bridged compounds are also distorted significantly, while those of the pentyl- and hexyl-bridged porphyrins are planar.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja00243a018</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>400201 - Chemical & Physicochemical Properties ; ABSORPTION SPECTROSCOPY ; Bioinorganic chemistry ; BOND LENGTHS ; CARBOXYLIC ACIDS ; CHEMICAL PREPARATION ; CHEMICAL SHIFT ; Chemistry ; COHERENT SCATTERING ; COMPLEXES ; Condensed matter: structure, mechanical and thermal properties ; CRYSTAL STRUCTURE ; DATA ; DIFFRACTION ; DIMENSIONS ; ELEMENTS ; Exact sciences and technology ; EXPERIMENTAL DATA ; HETEROCYCLIC ACIDS ; HETEROCYCLIC COMPOUNDS ; HYDROGEN ; INFORMATION ; Inorganic chemistry and origins of life ; Inorganic compounds ; INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY ; ISOMERS ; LENGTH ; MAGNETIC RESONANCE ; Metal complexes ; NMR SPECTRA ; NONMETALS ; NUCLEAR MAGNETIC RESONANCE ; NUMERICAL DATA ; ORGANIC ACIDS ; ORGANIC COMPOUNDS ; ORGANIC NITROGEN COMPOUNDS ; Physics ; PORPHYRINS ; RESONANCE ; SCATTERING ; SPACE GROUPS ; SPECTRA ; SPECTROSCOPY ; Structure of solids and liquids; crystallography ; Structure of specific crystalline solids ; SYNTHESIS ; ULTRAVIOLET SPECTRA ; VISIBLE SPECTRA ; X-RAY DIFFRACTION ; ZINC COMPLEXES</subject><ispartof>J. Am. Chem. Soc.; (United States), 1987-04, Vol.109 (9), p.2659-2668</ispartof><rights>1987 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a359t-5b6450c99a686a28fa8c02354410b8250d8ecb9dd60d45590c7114b12e8a6dd13</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ja00243a018$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja00243a018$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,885,2763,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=8166011$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/biblio/6541079$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Simonis, Ursula</creatorcontrib><creatorcontrib>Walker, F. Ann</creatorcontrib><creatorcontrib>Lee, Patricia Lani</creatorcontrib><creatorcontrib>Hanquet, Bernard J</creatorcontrib><creatorcontrib>Meyerhoff, Dieter J</creatorcontrib><creatorcontrib>Scheidt, W. Robert</creatorcontrib><creatorcontrib>San Francisco State Univ., CA</creatorcontrib><title>Synthesis, spectroscopic, and structural studies of extremely short chain basket handle porphyrins and their zinc(II) complexes</title><title>J. Am. Chem. Soc.; (United States)</title><addtitle>J. Am. Chem. Soc</addtitle><description>The synthesis of extremely short chain basket handle porphyrins is described. These molecules are derived from 5,10,15,20-tetraphenyl-21H,23H-porphine bearing alkoxy chains (handles) of 4-, 5-, and 6-carbon atoms covalently attached at the o-phenyl positions. For the n = 5 and 6 free base porphyrins three different isomers are formed: cross-trans-linked (I), adjacent-trans-linked (II) and adjacent-cis-linked (III) isomers. For the butyl-bridged compound only the latter two could be obtained. Attempts to insert zinc(II) ion into the porphinato cores have been successful only for isomers II and III; isomer I could not be metalated. The structural assignment of the three different isomers is based on UV-vis and /sup 1/H NMR spectroscopy as well as on X-ray structure analysis of the Zn(II) complex of the hexyl-bridged isomer II. The Zn hexyl II complex crystallizes in the monoclinic system, space group P2/sub 1//n, and cell dimensions at 296 K of a = 8.608 (2) A, b = 22.212 (4) A, c = 13.774 (2) A, and ..beta.. = 91.90 (1)/sup 0/ with two molecules per unit cell. The average Zn-N bond distance is 2.031 (3) A with the zinc atom precisely centered in the porphinato plane. On the basis of the spectroscopic and preliminary structural data, it is shown that the porphyrin ring of isomer I is permanently distorted from planarity. Furthermore, from analysis of spectroscopic data for isomers II and III it appears likely that the porphyrin rings of the butyl-bridged compounds are also distorted significantly, while those of the pentyl- and hexyl-bridged porphyrins are planar.</description><subject>400201 - Chemical & Physicochemical Properties</subject><subject>ABSORPTION SPECTROSCOPY</subject><subject>Bioinorganic chemistry</subject><subject>BOND LENGTHS</subject><subject>CARBOXYLIC ACIDS</subject><subject>CHEMICAL PREPARATION</subject><subject>CHEMICAL SHIFT</subject><subject>Chemistry</subject><subject>COHERENT SCATTERING</subject><subject>COMPLEXES</subject><subject>Condensed matter: structure, mechanical and thermal properties</subject><subject>CRYSTAL STRUCTURE</subject><subject>DATA</subject><subject>DIFFRACTION</subject><subject>DIMENSIONS</subject><subject>ELEMENTS</subject><subject>Exact sciences and technology</subject><subject>EXPERIMENTAL DATA</subject><subject>HETEROCYCLIC ACIDS</subject><subject>HETEROCYCLIC COMPOUNDS</subject><subject>HYDROGEN</subject><subject>INFORMATION</subject><subject>Inorganic chemistry and origins of life</subject><subject>Inorganic compounds</subject><subject>INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY</subject><subject>ISOMERS</subject><subject>LENGTH</subject><subject>MAGNETIC RESONANCE</subject><subject>Metal complexes</subject><subject>NMR SPECTRA</subject><subject>NONMETALS</subject><subject>NUCLEAR MAGNETIC RESONANCE</subject><subject>NUMERICAL DATA</subject><subject>ORGANIC ACIDS</subject><subject>ORGANIC COMPOUNDS</subject><subject>ORGANIC NITROGEN COMPOUNDS</subject><subject>Physics</subject><subject>PORPHYRINS</subject><subject>RESONANCE</subject><subject>SCATTERING</subject><subject>SPACE GROUPS</subject><subject>SPECTRA</subject><subject>SPECTROSCOPY</subject><subject>Structure of solids and liquids; crystallography</subject><subject>Structure of specific crystalline solids</subject><subject>SYNTHESIS</subject><subject>ULTRAVIOLET SPECTRA</subject><subject>VISIBLE SPECTRA</subject><subject>X-RAY DIFFRACTION</subject><subject>ZINC COMPLEXES</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1987</creationdate><recordtype>article</recordtype><recordid>eNptkFGL1DAQx4MouJ4--QWCCHp41aRt0vRRF08XDjy4lXsM6TSl2esmJZOFXV_uq5uzcvjg08wwv_nPzJ-Q15x95Kzkn3aGsbKuDOPqCVlxUbJC8FI-JSuWG0WjZPWcvEDc5bIuFV-R-5uTT6NFhxcUZwspBoQwO7igxvcUUzxAOkQz5fTQO4s0DNQeU7R7O50ojiEmCqNxnnYG72yiY56bLJ1DnMdTdB7_COUdLtJfzsP7zeacQtjPkz1afEmeDWZC--pvPCM_L79u19-Lqx_fNuvPV4WpRJsK0claMGhbI5U0pRqMAlZWoq4561QpWK8sdG3fS9bXQrQMGs7rjpdWGdn3vDojbxbdgMlpBJcsjBC8zy9rKbJM02bowwJBdgGjHfQc3d7Ek-ZMPxis_zE4028XejYIZhqi8eDwcURxKRl_2FwsmMNkj49tE--0bKpG6O31jW7W119uxfZWX2b-3cIbQL0Lh-izL_894DdzpJd3</recordid><startdate>19870401</startdate><enddate>19870401</enddate><creator>Simonis, Ursula</creator><creator>Walker, F. Ann</creator><creator>Lee, Patricia Lani</creator><creator>Hanquet, Bernard J</creator><creator>Meyerhoff, Dieter J</creator><creator>Scheidt, W. Robert</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>OTOTI</scope></search><sort><creationdate>19870401</creationdate><title>Synthesis, spectroscopic, and structural studies of extremely short chain basket handle porphyrins and their zinc(II) complexes</title><author>Simonis, Ursula ; Walker, F. Ann ; Lee, Patricia Lani ; Hanquet, Bernard J ; Meyerhoff, Dieter J ; Scheidt, W. Robert</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a359t-5b6450c99a686a28fa8c02354410b8250d8ecb9dd60d45590c7114b12e8a6dd13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1987</creationdate><topic>400201 - Chemical & Physicochemical Properties</topic><topic>ABSORPTION SPECTROSCOPY</topic><topic>Bioinorganic chemistry</topic><topic>BOND LENGTHS</topic><topic>CARBOXYLIC ACIDS</topic><topic>CHEMICAL PREPARATION</topic><topic>CHEMICAL SHIFT</topic><topic>Chemistry</topic><topic>COHERENT SCATTERING</topic><topic>COMPLEXES</topic><topic>Condensed matter: structure, mechanical and thermal properties</topic><topic>CRYSTAL STRUCTURE</topic><topic>DATA</topic><topic>DIFFRACTION</topic><topic>DIMENSIONS</topic><topic>ELEMENTS</topic><topic>Exact sciences and technology</topic><topic>EXPERIMENTAL DATA</topic><topic>HETEROCYCLIC ACIDS</topic><topic>HETEROCYCLIC COMPOUNDS</topic><topic>HYDROGEN</topic><topic>INFORMATION</topic><topic>Inorganic chemistry and origins of life</topic><topic>Inorganic compounds</topic><topic>INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY</topic><topic>ISOMERS</topic><topic>LENGTH</topic><topic>MAGNETIC RESONANCE</topic><topic>Metal complexes</topic><topic>NMR SPECTRA</topic><topic>NONMETALS</topic><topic>NUCLEAR MAGNETIC RESONANCE</topic><topic>NUMERICAL DATA</topic><topic>ORGANIC ACIDS</topic><topic>ORGANIC COMPOUNDS</topic><topic>ORGANIC NITROGEN COMPOUNDS</topic><topic>Physics</topic><topic>PORPHYRINS</topic><topic>RESONANCE</topic><topic>SCATTERING</topic><topic>SPACE GROUPS</topic><topic>SPECTRA</topic><topic>SPECTROSCOPY</topic><topic>Structure of solids and liquids; crystallography</topic><topic>Structure of specific crystalline solids</topic><topic>SYNTHESIS</topic><topic>ULTRAVIOLET SPECTRA</topic><topic>VISIBLE SPECTRA</topic><topic>X-RAY DIFFRACTION</topic><topic>ZINC COMPLEXES</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Simonis, Ursula</creatorcontrib><creatorcontrib>Walker, F. Ann</creatorcontrib><creatorcontrib>Lee, Patricia Lani</creatorcontrib><creatorcontrib>Hanquet, Bernard J</creatorcontrib><creatorcontrib>Meyerhoff, Dieter J</creatorcontrib><creatorcontrib>Scheidt, W. Robert</creatorcontrib><creatorcontrib>San Francisco State Univ., CA</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>OSTI.GOV</collection><jtitle>J. Am. Chem. Soc.; (United States)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Simonis, Ursula</au><au>Walker, F. Ann</au><au>Lee, Patricia Lani</au><au>Hanquet, Bernard J</au><au>Meyerhoff, Dieter J</au><au>Scheidt, W. Robert</au><aucorp>San Francisco State Univ., CA</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, spectroscopic, and structural studies of extremely short chain basket handle porphyrins and their zinc(II) complexes</atitle><jtitle>J. Am. Chem. Soc.; (United States)</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>1987-04-01</date><risdate>1987</risdate><volume>109</volume><issue>9</issue><spage>2659</spage><epage>2668</epage><pages>2659-2668</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>The synthesis of extremely short chain basket handle porphyrins is described. These molecules are derived from 5,10,15,20-tetraphenyl-21H,23H-porphine bearing alkoxy chains (handles) of 4-, 5-, and 6-carbon atoms covalently attached at the o-phenyl positions. For the n = 5 and 6 free base porphyrins three different isomers are formed: cross-trans-linked (I), adjacent-trans-linked (II) and adjacent-cis-linked (III) isomers. For the butyl-bridged compound only the latter two could be obtained. Attempts to insert zinc(II) ion into the porphinato cores have been successful only for isomers II and III; isomer I could not be metalated. The structural assignment of the three different isomers is based on UV-vis and /sup 1/H NMR spectroscopy as well as on X-ray structure analysis of the Zn(II) complex of the hexyl-bridged isomer II. The Zn hexyl II complex crystallizes in the monoclinic system, space group P2/sub 1//n, and cell dimensions at 296 K of a = 8.608 (2) A, b = 22.212 (4) A, c = 13.774 (2) A, and ..beta.. = 91.90 (1)/sup 0/ with two molecules per unit cell. The average Zn-N bond distance is 2.031 (3) A with the zinc atom precisely centered in the porphinato plane. On the basis of the spectroscopic and preliminary structural data, it is shown that the porphyrin ring of isomer I is permanently distorted from planarity. Furthermore, from analysis of spectroscopic data for isomers II and III it appears likely that the porphyrin rings of the butyl-bridged compounds are also distorted significantly, while those of the pentyl- and hexyl-bridged porphyrins are planar.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><doi>10.1021/ja00243a018</doi><tpages>10</tpages></addata></record> |
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| ispartof | J. Am. Chem. Soc.; (United States), 1987-04, Vol.109 (9), p.2659-2668 |
| issn | 0002-7863 1520-5126 |
| language | eng |
| recordid | cdi_crossref_primary_10_1021_ja00243a018 |
| source | ACS Publications |
| subjects | 400201 - Chemical & Physicochemical Properties ABSORPTION SPECTROSCOPY Bioinorganic chemistry BOND LENGTHS CARBOXYLIC ACIDS CHEMICAL PREPARATION CHEMICAL SHIFT Chemistry COHERENT SCATTERING COMPLEXES Condensed matter: structure, mechanical and thermal properties CRYSTAL STRUCTURE DATA DIFFRACTION DIMENSIONS ELEMENTS Exact sciences and technology EXPERIMENTAL DATA HETEROCYCLIC ACIDS HETEROCYCLIC COMPOUNDS HYDROGEN INFORMATION Inorganic chemistry and origins of life Inorganic compounds INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY ISOMERS LENGTH MAGNETIC RESONANCE Metal complexes NMR SPECTRA NONMETALS NUCLEAR MAGNETIC RESONANCE NUMERICAL DATA ORGANIC ACIDS ORGANIC COMPOUNDS ORGANIC NITROGEN COMPOUNDS Physics PORPHYRINS RESONANCE SCATTERING SPACE GROUPS SPECTRA SPECTROSCOPY Structure of solids and liquids crystallography Structure of specific crystalline solids SYNTHESIS ULTRAVIOLET SPECTRA VISIBLE SPECTRA X-RAY DIFFRACTION ZINC COMPLEXES |
| title | Synthesis, spectroscopic, and structural studies of extremely short chain basket handle porphyrins and their zinc(II) complexes |
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