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Photosensitized singlet oxygen and its applications

Maria C DeRosa, Robert J Crutchley

Department of Chemistry, Ottawa-Carleton Chemistry Institute, Carleton University, 22 ! "er#ber$ %uil&in$, ''2( Colonel %y Drive, Ottawa, O), Cana&a *'+ (%, http-..&/0&oi0or$.'!0'!',.+!!'!-1( (2!23!!!4 -,, "ow to Cite or 5in6 Usin$ DOI 7ermissions 8 Reprints

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Abstract
;he stu&y of sin$let molecular o/y$en pro&uction an& reactivity has emer$e& as a rich an& &iverse area with implications in fiel&s ran$in$ from polymer science to cancer therapy0 In this review, we a&&ress the photophysical properties of sin$let o/y$en an& of the photosensiti#ers use& in its $eneration0 7hotosensiti#ers base& on or$anic molecules an& coor&ination compoun&s are e/amine& an& compare&0 Recent a&vances in the photosensiti#e& pro&uction of sin$let o/y$en an& its uses in photochemistry an& photobiolo$y are hi$hli$hte&, with particular focus on its role in wastewater treatment, fine chemical synthesis, an& photo&ynamic therapy 27D;30 <uture &irections in photosensiti#er &evelopment an& sin$let o/y$en applications are also e/plore&0

Keywords

+in$let o/y$en= 7hotosensiti#ers= 7hoto&ynamic therapy

<i$ures an& tables from this article-

<i$0 '0 7otential ener$y curves for the three low-lyin$ electronic states of molecular o/y$en0 <i$ure options

<i$0 20 7rimitive representations of molecular o/y$en lowest sin$let an& triplet states0 <i$ure options

<i$0 40 >eneration of e/cite& photosensiti#er states an& reactive &io/y$en species0 ?Repro&uce& with permission from Ref0 ?44@0 Copyri$ht 2'AA(3 Royal Chemical +ociety0@ <i$ure options

<i$0 0 +ome common or$anic photosensiti#ers0 <i$ure options

<i$0 (0 <ormation of methyl oleate hy&ropero/i&es 2'1-' Me-OO"3 &urin$ the photoo/i&ation of methyl oleate 2'!! BM3 in ethanol in the presence of '! m$ mlC' ;iO2 or !0( m$ mlC' DnO un&er aerobic con&itions at room temperature0 ?Repro&uce& with permission from Ref0 ? E@0 Copyri$ht 22!!!3 Fca&emic 7ress0@ <i$ure options

<i$0 ,0 <ormation of -o/o-;GM7O upon irra&iation of -o/o-;M7 with '0, m$ mlC' ;iO2 or DnO at room temperature un&er aerobic con&itions0 ?Repro&uce& with permission from Ref0 ? E@0 Copyri$ht 22!!!3 Fca&emic 7ress0@ <i$ure options

<i$0 E0 7hotoo/i&ation of ' mmol of citronellol in methanol with immobili#e& rose ben$al on Fmberlite IRF !! employe& nine times0 ?Repro&uce& with permission from Ref0 ?('@0 Copyri$ht 22!!'3 John Hiley an& +ons0@ <i$ure options

<i$0 10 7hotoo/i&ation of ' mmol of citronellol in methanol usin$ immobili#e& +i27c;+3 2O"32 on Fmberlite IRF !! employe& nine times0 ?Repro&uce& with permission from Ref0 ?('@0 Copyri$ht 22!!'3 John Hiley an& +ons0@ <i$ure options

<i$0 A0 Repeate& cyclopenta&iene 2C73 photoo/i&ation e/periments usin$ C'2I7im as the photosensiti#er 2?Ru2II3@J(0!K'!C( M= ?C7@J20(K'!C2 M30 Irra&iation time of one cycle

was 2! min in runs 'LA an& 4! min in runs '! an& ''0 ?Repro&uce& with permission from Ref0 ?(4@0 Copyri$ht 2'AAA3 Chemical +ociety of Japan0@ <i$ure options

<i$0 '!0 ;he photoo/i&ation of ' mmol of cyclopenta&iene in ethanol with immobili#e& photosensiti#ers0 21bJDn7c;+= 2bJFl2O"37c;+= 3bJ>a2O"37c;+= 4bJ+i2O"327c;+= 5bJ>e2O"327c;+30 ?Repro&uce& with permission from Ref0 ?('@0 Copyri$ht 22!!'3 John Hiley an& +ons0@ <i$ure options

<i$0 ''0 Chan$es in the concentration of phenol upon irra&iation of aMueous solutions of 7+++-9%C.R% an& phenol at various p"0 2a3 p" E02= 2b3 '!04= an& 2c3 ''040 ?Repro&uce& with permission from Ref0 ? A@0 Copyri$ht 2'AA13 Glsevier +cience0@ <i$ure options

<i$0 '20 7hotoo/i&ation of !04, mmol of phenol in aMueous solutions at p" '! with &ifferent immobili#e& photosensiti#ers0 1bJDn7c;+= 2bJFl2O"37c;+= 3bJ>a2O"37c;+= 4bJ+i2O"327c;+= 5bJ>e2O"327c;+= 6bJrose ben$al0 ?Repro&uce& with permission from Ref0 ?('@0 Copyri$ht 22!!'3 John Hiley an& +ons0@ <i$ure options

<i$0 '40 7hotoo/i&ation of !0E' mmol of so&ium sulfi&e usin$ !0( Bmol of &ifferent catalysts in solutions containin$ !0' M C;FC0 2'3 Dn2II37c;+= 223 Fl2III32O"37c;+= 243 Fl2III32O"37c;+ without C;FC= 2 3 "27c;+= 2(3 Co2II37c;+= 2,3 Co2II37c;+ 2not

irra&iate&30 ?Repro&uce& with permission from Ref0 ?,'@0 Copyri$ht 2'AA13 Glsevier +cience0@ <i$ure options

<i$0 ' 0 7hotosensiti#er absorbance compare& to tissue transmittance0 ;he +oret, an& I, II, III, I9 ban&s represent those of porphyrin0 ;he transmittance curve is obtaine& from a sample of human scrotal sac 2E mm thic630 ;he broa& absorbance from (!! to ,!! nm is attribute& to haemo$lobin0 ?Repro&uce& with permission from Ref0 ?44@0 Copyri$ht 2'AA(3 Royal Chemical +ociety0@ <i$ure options

<i$0 '(0 Fbsorption spectra of m-;"77 2soli& line3, m-;"7C 2small &ashe& line3, an& m;"7%C 2lar$e &ashe& line30 ?Repro&uce& with permission from Ref0 ?44@0 Copyri$ht 2'AA(3 Royal Chemical +ociety0@ <i$ure options

<i$0 ',0 Reaction scheme for the selective attachment of thir&-$eneration photosensiti#ers to the surface of a tumor cell 2+F, streptavi&in= b7+, biotinylate& photosensiti#er30 ?Repro&uce& with permission from Ref0 ?2A@0 Copyri$ht 2'AA13 *luwer0@ <i$ure options

<i$0 'E0 7ercent survival of three &iptera Ceratitis capitata 2circles3, Bactrocera 2Dacus3 oleae 2K3, an& Stomoxys calcitrans 2sMuares3 after ' h irra&iation with white li$ht0 ;he

flies ha& been e/pose& to a bait containin$ 1 BM haematoporphyrin0 ?Repro&uce& with permission from Ref0 ?1(@0 Copyri$ht 22!!!3 Glsevier +cience0@ <i$ure options ;able '0 +ome e/amples ?24@ of common or$anic &yes an& their photophysical properties

9iew Hithin Frticle ;able 20 7hotophysical properties for some metalloporphyrins an&

9iew Hithin Frticle ;able 40 7hotophysical properties of some metal phthalocyanines an&

9iew Hithin Frticle ;able 0 +in$let o/y$en Muantum yiel&s for a ran$e of &iama$netic an& parama$netic te/aphyrin comple/es

<i$ure options 9iew Hithin Frticle ;able (0 Iuantum yiel&s of sin$let o/y$en formation of several Ru2II3 comple/es

9iew Hithin Frticle ;able ,0 7hotophysical an& biolo$ical properties of a series of chlorin an& porphyrin &imers

9iew Hithin Frticle

;able E0 Comparison of the photophysical properties of the first an& secon& $enerations of photosensiti#ers an&

9iew Hithin Frticle