The synthesis and photocleavage of quinolinyl methyl ether-protected alcohols is reported in this study. A variety of quinoline methyl chlorides were synthesized, and protection of the various alcohols was performed via a substitution reaction in the presence of a strong base. Photocleavage of the quinolinyl methyl ether moiety proceeded under visible light with the formation of the charged quinolinyl radical intermediate through a single-electron transfer in the presence of a photosensitizer dye leading to the deprotected alcohol in excellent yields. The utility of triethylamine as a sacrificial reductant and d-sorbitol as a radical scavenger were also investigated in this study.

The regioselective cleavage of epoxides using visible light and a catalytic dye is reported in this study as an alternative mild synthetic approach. The epoxide radical anion is generated via visible light in an electron transfer reaction, induced by non-toxic dyes, leading to ring opening and formation of the corresponding alcohol with the hydroxyl group on the less substituted carbon in excellent yields.

Acetonitrile is a commonly used solvent in both industry and research. The treatment of acetonitrile wastes in dilute aqueous solutions with visible light offers advantages to chemical treatment and ultraviolet (UV) irradiation. This study presents the degradation of acetonitrile via a photoinduced electron transfer reaction in the presence of a photosensitizer (dye) and a sacrificial reductant under visible light. Acetonitrile photodegradation (photoreduction) was investigated utilizing a variety of sacrificial reductants and photosensitizers. Optimal results were observed in the presence of methylene green and tri-isopropanolamine with a decrease of acetonitrile in solution to 86% in 24hours. The only photoreaction product observed was acetaldehyde and a plausible mechanism for the photochemical degradation of acetonitrile is proposed.

ADVERTISEMENT RETURN TO ISSUEPREVCommunication to the...Communication to the EditorNEXT3-Dimensional Submicron Polymerization of Acrylamide by Multiphoton Excitation of Xanthene DyesPaul J. Campagnola, David M. Delguidice, Gary A. Epling, Kurt D. Hoffacker, Amy R. Howell, Jonathan D. Pitts, and Steven L. GoodmanView Author Information Department of Physiology and Center for Biomedical Imaging Technology, University of Connecticut Health Center, Farmington, Connecticut 06030, Department of Chemistry, Stamford High, Stamford, Connecticut, Department of Chemistry, University of Connecticut, Storrs, Connecticut, and Center for Biomaterials, University of Connecticut Health Center, Farmington, Connecticut 06030 Cite this: Macromolecules 2000, 33, 5, 1511–1513Publication Date (Web):February 4, 2000Publication History Received29 June 1999Revised9 November 1999Published online4 February 2000Published inissue 1 March 2000https://doi.org/10.1021/ma991042eCopyright © 2000 American Chemical SocietyRIGHTS & PERMISSIONSArticle Views976Altmetric-Citations83LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit Read OnlinePDF (89 KB) Get e-AlertsSUBJECTS:Fluorescence,Lasers,Manufacturing,Polymerization,Power Get e-Alerts

Nonlinear multiphoton photo-cross-linking and photopolymerization of proteins and polymers in solution have been used to direct the three-dimensional assembly of micron scale objects. Two aspects of fabricated proteinatious matrixes are examined in this paper: the efficiency of protein photopolymerization and the application of fabricated matrixes as sustained release devices. The efficiency of photoactivated cross-linking of the proteins bovine serum albumin and fibrinogen, using rose bengal, have been determined and found to vary with photosensitizer concentration. This concentration dependence suggests that the mechanism for protein cross-linking is a direct hydrogen transfer between an amino acid residue of the protein and the dye molecule itself. A comparison of the surface structure of single and multiple protein oligomers is undertaken and shown to Vary significantly depending on fabrication materials. Alkaline phosphatase bioactivity, upon entrapment in a protein structure, is maintained. The properties of fabricated protein matrixes as sustained release devices is also examined. The rates of diffusion of fluorescently labeled dextrans (10 and 40 kDa) from an optically fabricated BSA matrix vary with molecular weight and are linear with cross-link density. The half-life of release of 10 kDa dextran-TMR from a BSA micron scale structure is less than or equal to 6 min while 40 kDa dextran-TMR half-life of release is 25 min. Finally, rhodamine 610, a typical drug size molecule, was entrapped in an acrylamide structure, and its release is found to be diffusion-limited with half-lives of 10-31 min, depending on cross-link density.

Methods to prevent pollution from toxic heavy metals have been explored through development of nontoxic catalytic alternatives for oxidation of dithianes, oxathianes, and benzyl ethers. Inexpensive spotlights were utilized to induce high-yield preparative scale photoreactions. In this manner, dye-sensitized irradiation of dithianes led to cleavage, generating a dithiol and a carbonyl compound, while oxathiane irradiation led to a carbonyl compound and a hydroxythiol. Trimethoxybenzyl ether irradiation produced an alcohol and an aromatic aldehyde. A single electron transfer mechanism seems responsible for initiating the bond cleavages that mimic electrochemical oxidation of these substrates. An advantage over electrochemistry, however, is that the dye-sensitized transformations are more conveniently scaled up. In this study multi-gram reactions have been performed without difficulty.

PD 117596 is a novel quinolone compound that is being investigated for use as an antibacterial agent. Early investigations demonstrated a significant phototoxic liability associated with this compound. These studies were undertaken to investigate the mechanism of phototoxicity using an in vitro model. In the UVA region, PD 117596 was found to be a more efficient producer of singlet oxygen than rose bengal, ciprofloxacin, nalidixic acid, or PD 118879, another quinolone under investigation. The quantum yield of photoreaction for PD 117596 was relatively low (φ = 0.021); however, it was approximately 10-fold higher than other tested quinolones. In vitro studies using a mouse erythrocyte model were used to further investigate the mechanism of phototoxicity. PD 117596-induced photohemolysis was found to be oxygen dependent with a relatively rapid onset that progressed even after removal of light. Preirradiation of the compound prevented subsequent hemolytic or photohemolytic action. BHA, BHT, α-tocopherol, and the iron chelator DTPA were all found to be effective at ameliorating the photohemolytic response. The photohemolytic response was markedly enhanced when D 2 O was substituted for H 2 O in the incubation medium, indicating a singlet oxygen-mediated mechanism of action. A rise in thiobarbituric acid products was noted within 1 hr of irradiation and was maximal at the time of onset of overt photohemolysis. These data suggest that singlet oxygen production by irradiated PD 117596 is responsible for secondary changes in mouse red blood cells including lipid peroxidation and ultimately results in cellular lysis.

Chemischer InformationsdienstVolume 16, Issue 12 Physical Organic Chemistry ChemInform Abstract: QUENCHING OF THE FLUORESCENCE OF QUINOLINE DERIVATIVES BY EXCIPLEX FORMATION WITH HETEROATOM-CONTAINING COMPOUNDS G. A. EPLING, G. A. EPLINGSearch for more papers by this authorK.-Y. LIN, K.-Y. LINSearch for more papers by this author G. A. EPLING, G. A. EPLINGSearch for more papers by this authorK.-Y. LIN, K.-Y. LINSearch for more papers by this author First published: March 26, 1985 https://doi.org/10.1002/chin.198512052AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume16, Issue12March 26, 1985 RelatedInformation

A new arylmethylsulfonyl chloride reacts with secondary or primary amines to give sulfonamides which can be photochemically cleaved, making it suitable for use as a photoremovable protecting group.

AbstractDie Belichtung von Quadricyclan (I) ergibt die Verbindungen (II) bis (IV).

Bei der Photolyse des Antimalaria‐Mittels Me?oquine (I), das im Gegensatz zu ähnlich strukturierten Verbindungen wie z.B. (IV) kaum zu lichtinduzierten Hautschädigungen′ führt, werden der Ester (II) und der Alkohol (III) erhalten.

Chemischer InformationsdienstVolume 8, Issue 27 Preparative Organic Chemistry ChemInform Abstract: FRAGMENTATION PATHWAYS IN THE PHOTOLYSIS OF PHENYLACETIC ACID G. A. EPLING, G. A. EPLINGSearch for more papers by this authorA. LOPES, A. LOPESSearch for more papers by this author G. A. EPLING, G. A. EPLINGSearch for more papers by this authorA. LOPES, A. LOPESSearch for more papers by this author First published: July 5, 1977 https://doi.org/10.1002/chin.197727119AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume8, Issue27July 5, 1977 RelatedInformation

AbstractIm Gegensatz zum Verhalten des Methylencyclohexens (V), dessen direkte Photolyse zur bicyclischen Verbindung (VI) und dessen sensibilisierte Bestrahlung zu keinen Produkten führt, liefert die acetonsensibilisierte Photolyse des Diens (III) das cis‐ und trans‐Bicyclohexen (II) und das trans‐Produkt (I), während durch direkte Bestrahlung das Trien (IV) und das trans‐Bicyclohexen (II) entstehen.

AbstractDie Behandlung des Ketons (I) mit K‐tert.‐butanolat bei Raumtemperatur, liefert eine Mischung der Phenole (II) und (III), die auch durch photochemische Umlagerung des Bicyclohexenons (IV) im gleichen Verhältnis entstehen.

AbstractPhotoisomerisierung von cis‐ in trans‐S,6‐Diphenyl‐bicyclo[3.1.0]hexen‐(2) und Photoisomerisierungbeider zu 4,5‐Diphenyl‐bicyclo[3.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTMechanistic and exploratory organic photochemistry. LV. Geometric control of multiplicity in the di-.pi.-methane rearrangementHoward E. Zimmerman and Gary A. EplingCite this: J. Am. Chem. Soc. 1970, 92, 5, 1411–1412Publication Date (Print):March 1, 1970Publication History Published online1 May 2002Published inissue 1 March 1970https://doi.org/10.1021/ja00708a057RIGHTS & PERMISSIONSArticle Views71Altmetric-Citations14LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (247 KB) Get e-Alerts Get e-Alerts