Chemiexcitation efficiency for the charge-transfer-induced chemiluminescent decomposition of 3-hydroxyphenyl-substituted dioxetanes in an aqueous system
The decomposition of 3-oxyphenyl-3-methoxy-4-(2′-spiroadamantane)-1,2-dioxetane (A) and 5-tert-butyl-4,4-dimethyl-1-(3-oxyphenyl)bicyclo[3.2.0]heptane (B) in NaOH/H2O gives light in poor yield, which is several orders of magnitude lower than that in aprotic solvents. To understand the poor chemilumi...
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| Veröffentlicht in: | Tetrahedron letters 2014-02, Vol.55 (9), p.1644-1647 |
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| creator | Watanabe, Nobuko Oguri, Azusa Horikoshi, Miho Takatsuka, Hikaru Ijuin, Hisako K. Matsumoto, Masakatsu |
| description | The decomposition of 3-oxyphenyl-3-methoxy-4-(2′-spiroadamantane)-1,2-dioxetane (A) and 5-tert-butyl-4,4-dimethyl-1-(3-oxyphenyl)bicyclo[3.2.0]heptane (B) in NaOH/H2O gives light in poor yield, which is several orders of magnitude lower than that in aprotic solvents. To understand the poor chemiluminescence efficiency in NaOH/H2O, we investigated the behaviors of the authentic emitters, methyl 3-oxidobenzoate (C) and 2,2,4,4-tetramethyl-3-oxopentyl 3-oxidobenzoate (D). We found that D was weakly fluorescent though hydrolyzed in NaOH/H2O, and estimated that the singlet-chemiexcitation efficiency ΦS was 6.1×10−3 for the decomposition of B in NaOH/H2O. On the other hand, ΦS for A could not be estimated, since C was hydrolyzed too rapidly to observe its fluorescence. |
| doi_str_mv | 10.1016/j.tetlet.2014.01.089 |
| format | Article |
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To understand the poor chemiluminescence efficiency in NaOH/H2O, we investigated the behaviors of the authentic emitters, methyl 3-oxidobenzoate (C) and 2,2,4,4-tetramethyl-3-oxopentyl 3-oxidobenzoate (D). We found that D was weakly fluorescent though hydrolyzed in NaOH/H2O, and estimated that the singlet-chemiexcitation efficiency ΦS was 6.1×10−3 for the decomposition of B in NaOH/H2O. On the other hand, ΦS for A could not be estimated, since C was hydrolyzed too rapidly to observe its fluorescence.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2014.01.089</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Aqueous system ; Chemiexcitation efficiency ; Chemiluminescence ; Decomposition ; Dioxetane ; Emitters ; Fluorescence ; Solvents ; Tetrahedrons</subject><ispartof>Tetrahedron letters, 2014-02, Vol.55 (9), p.1644-1647</ispartof><rights>2014 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c405t-dd1a48977f68d5774fb68c99f9b06aafc314d1dbbe8771a802564b71614be5de3</citedby><cites>FETCH-LOGICAL-c405t-dd1a48977f68d5774fb68c99f9b06aafc314d1dbbe8771a802564b71614be5de3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tetlet.2014.01.089$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27922,27923,45993</link.rule.ids></links><search><creatorcontrib>Watanabe, Nobuko</creatorcontrib><creatorcontrib>Oguri, Azusa</creatorcontrib><creatorcontrib>Horikoshi, Miho</creatorcontrib><creatorcontrib>Takatsuka, Hikaru</creatorcontrib><creatorcontrib>Ijuin, Hisako K.</creatorcontrib><creatorcontrib>Matsumoto, Masakatsu</creatorcontrib><title>Chemiexcitation efficiency for the charge-transfer-induced chemiluminescent decomposition of 3-hydroxyphenyl-substituted dioxetanes in an aqueous system</title><title>Tetrahedron letters</title><description>The decomposition of 3-oxyphenyl-3-methoxy-4-(2′-spiroadamantane)-1,2-dioxetane (A) and 5-tert-butyl-4,4-dimethyl-1-(3-oxyphenyl)bicyclo[3.2.0]heptane (B) in NaOH/H2O gives light in poor yield, which is several orders of magnitude lower than that in aprotic solvents. To understand the poor chemiluminescence efficiency in NaOH/H2O, we investigated the behaviors of the authentic emitters, methyl 3-oxidobenzoate (C) and 2,2,4,4-tetramethyl-3-oxopentyl 3-oxidobenzoate (D). We found that D was weakly fluorescent though hydrolyzed in NaOH/H2O, and estimated that the singlet-chemiexcitation efficiency ΦS was 6.1×10−3 for the decomposition of B in NaOH/H2O. On the other hand, ΦS for A could not be estimated, since C was hydrolyzed too rapidly to observe its fluorescence.</description><subject>Aqueous system</subject><subject>Chemiexcitation efficiency</subject><subject>Chemiluminescence</subject><subject>Decomposition</subject><subject>Dioxetane</subject><subject>Emitters</subject><subject>Fluorescence</subject><subject>Solvents</subject><subject>Tetrahedrons</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNp9kcGKFDEQhoMoOK6-gYccvaRNTac76Ysgg67Cghc9h3RSsTN0d8YkLdNv4uOa3fFsESgo6vv5Kz8hb4E3wKF_f24KlhlLc-QgGg4NV8MzcgAlW9Z2Cp6TA-eCM8Hb4SV5lfOZ1-oVP5A_pwmXgFcbiikhrhS9DzbganfqY6JlQmonk34iK8ms2WNiYXWbRVfnFZ23JayYLa6FOrRxucQcnpSipy2bdpfidb9MuO4zy9uYSyhbqbQL8YrFVJaGlZr6fm0Yt0zzngsur8kLb-aMb_71O_Lj86fvpy_s4dv919PHB2YF7wpzDoxQg5S-V66TUvixV3YY_DDy3hhvWxAO3DiikhKM4seuF6OEHsSIncP2jry76V5SrAZy0Uuo18xzdVbdaJBC9IM6gqir4rZqU8w5odeXFBaTdg1cPwahz_oWhH4MQnPQNYiKfbhhWM_4HTDp_PTB6EJCW7SL4f8CfwFUH5lY</recordid><startdate>20140226</startdate><enddate>20140226</enddate><creator>Watanabe, Nobuko</creator><creator>Oguri, Azusa</creator><creator>Horikoshi, Miho</creator><creator>Takatsuka, Hikaru</creator><creator>Ijuin, Hisako K.</creator><creator>Matsumoto, Masakatsu</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20140226</creationdate><title>Chemiexcitation efficiency for the charge-transfer-induced chemiluminescent decomposition of 3-hydroxyphenyl-substituted dioxetanes in an aqueous system</title><author>Watanabe, Nobuko ; Oguri, Azusa ; Horikoshi, Miho ; Takatsuka, Hikaru ; Ijuin, Hisako K. ; Matsumoto, Masakatsu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c405t-dd1a48977f68d5774fb68c99f9b06aafc314d1dbbe8771a802564b71614be5de3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Aqueous system</topic><topic>Chemiexcitation efficiency</topic><topic>Chemiluminescence</topic><topic>Decomposition</topic><topic>Dioxetane</topic><topic>Emitters</topic><topic>Fluorescence</topic><topic>Solvents</topic><topic>Tetrahedrons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Watanabe, Nobuko</creatorcontrib><creatorcontrib>Oguri, Azusa</creatorcontrib><creatorcontrib>Horikoshi, Miho</creatorcontrib><creatorcontrib>Takatsuka, Hikaru</creatorcontrib><creatorcontrib>Ijuin, Hisako K.</creatorcontrib><creatorcontrib>Matsumoto, Masakatsu</creatorcontrib><collection>CrossRef</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>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Watanabe, Nobuko</au><au>Oguri, Azusa</au><au>Horikoshi, Miho</au><au>Takatsuka, Hikaru</au><au>Ijuin, Hisako K.</au><au>Matsumoto, Masakatsu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemiexcitation efficiency for the charge-transfer-induced chemiluminescent decomposition of 3-hydroxyphenyl-substituted dioxetanes in an aqueous system</atitle><jtitle>Tetrahedron letters</jtitle><date>2014-02-26</date><risdate>2014</risdate><volume>55</volume><issue>9</issue><spage>1644</spage><epage>1647</epage><pages>1644-1647</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>The decomposition of 3-oxyphenyl-3-methoxy-4-(2′-spiroadamantane)-1,2-dioxetane (A) and 5-tert-butyl-4,4-dimethyl-1-(3-oxyphenyl)bicyclo[3.2.0]heptane (B) in NaOH/H2O gives light in poor yield, which is several orders of magnitude lower than that in aprotic solvents. To understand the poor chemiluminescence efficiency in NaOH/H2O, we investigated the behaviors of the authentic emitters, methyl 3-oxidobenzoate (C) and 2,2,4,4-tetramethyl-3-oxopentyl 3-oxidobenzoate (D). We found that D was weakly fluorescent though hydrolyzed in NaOH/H2O, and estimated that the singlet-chemiexcitation efficiency ΦS was 6.1×10−3 for the decomposition of B in NaOH/H2O. On the other hand, ΦS for A could not be estimated, since C was hydrolyzed too rapidly to observe its fluorescence.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2014.01.089</doi><tpages>4</tpages></addata></record> |
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| subjects | Aqueous system Chemiexcitation efficiency Chemiluminescence Decomposition Dioxetane Emitters Fluorescence Solvents Tetrahedrons |
| title | Chemiexcitation efficiency for the charge-transfer-induced chemiluminescent decomposition of 3-hydroxyphenyl-substituted dioxetanes in an aqueous system |
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