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Special Issue "Photochemistry in Organic Synthesis"

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Synthesis".

Deadline for manuscript submissions: closed (31 March 2010)

Special Issue Editor

Guest Editor
Dr. Joaquim Luís Faria

Laboratory of Catalysis and Materials, Department of Chemical Engineering, Faculty of Engineering, University of Porto, Rua Doutor Roberto Frias s/n, 4200-465 Porto, Portugal
E-Mail
Fax: +351 225 081 449
Interests: photochemistry and photocatalysis: photoinduced electron and energy transfer processes; heterogeneous photocatalysis and photocatalytic reactor engineering; photocatalytic processes (homogeneous and heterogeneous); catalysis and kinetics: selective hydrogenation in liquid phase; catalytic wet air oxidation; advanced oxidation processes for air and water treatments; spectroscopy: time resolved analysis of short lived intermediates; materials characterization; surface reactions; interface analysis by non-linear spectroscopy

Special Issue Information

Dear Colleagues,

Photochemistry in Organic Synthesis concerns any type of useful chemical reaction that can by initiated by one electronic excited state of an organic molecule, generated after irradiation of a suitable system in the UV or visible region. In our days, because of environmental concerns, conversion to a highly functional compound by a photochemical useful reaction needs to be encompassed with a high selectivity to minimize waste. Thus, in this issue in addition to the traditional fields of electronic excited state reactivity and conventional photoinduced electron transfer activation, attention will be given to the enormous potential of photocatalysis as a tool for sustainable organic synthesis. Since radiation sources, optical materials and spectroscopic analytical tools are rapidly evolving, technological aspects as photochemical reactor engineering will be also covered.

Dr. Joaquim Luís Faria
Guest Editor

Keywords

  • electronic photo-excited states
  • energy transfer
  • photocatalysis
  • photochemical organic synthesis
  • photochemistry
  • photoinduced electron transfer
  • selective photo-oxidation
  • selective photo-reduction
  • semiconductor photocatalysis

Published Papers (8 papers)

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Research

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Open AccessArticle Syntheses, Characterization, and Photo-Hydrogen-Evolving Properties of Tris(2,2'-bipyridine)ruthenium(II) Derivatives Tethered to an H2-Evolving (2-phenylpyridinato)platinum(II) Unit
Molecules 2010, 15(7), 4908-4923; doi:10.3390/molecules15074908
Received: 25 May 2010 / Revised: 1 July 2010 / Accepted: 14 July 2010 / Published: 14 July 2010
Cited by 16 | PDF Full-text (800 KB)
Abstract
With the aim of developing new molecular devices having higher photo-hydrogen-evolving activity, Pt(ppy)ClX units (ppy = 2-phenylpyridinate, X = Cl- or DMSO; DMSO = dimethylsulfoxide) have been employed as an H2-evolving site, as the catalytic activity of [Pt(ppy)Cl2]
[...] Read more.
With the aim of developing new molecular devices having higher photo-hydrogen-evolving activity, Pt(ppy)ClX units (ppy = 2-phenylpyridinate, X = Cl- or DMSO; DMSO = dimethylsulfoxide) have been employed as an H2-evolving site, as the catalytic activity of [Pt(ppy)Cl2]- was confirmed to be higher than those of other mononuclear platinum(II) complexes. In the present study, two new heterodinuclear Ru(II)Pt(II) complexes, produced by condensation of [Ru(bpy)2(5-amino-phen)]2+ (bpy = 2,2'-bipyridine, phen = 1,10-phenanthroline) with [Pt(cppy)Cl2]- and Pt(cppy)(DMSO)Cl (cppy = 9-carboxy-phenylpyridinate), respectively, have been prepared and their photo-hydrogen-evolving activities have been evaluated in detail. The ineffectiveness of these systems as photo-hydrogen-evolving molecular devices are interpreted in terms of their negative driving forces for the photoinduced electron transfer from the triplet MLCT excited state of the Ru chromophore to the p*(ppy) orbital of the catalyst moiety. Full article
(This article belongs to the Special Issue Photochemistry in Organic Synthesis)
Open AccessArticle Photochemical Synthesis of Nucleoside Analogues from Cyclobutanones: Bicyclic and Isonucleosides
Molecules 2010, 15(6), 3816-3828; doi:10.3390/molecules15063816
Received: 8 April 2010 / Revised: 19 May 2010 / Accepted: 24 May 2010 / Published: 26 May 2010
Cited by 3 | PDF Full-text (252 KB)
Abstract
The preparation of two nucleoside analogues are reported. Both syntheses involve a key photochemical ring-expansion of cyclobutanones to an oxacarbene and its subsequent scavenging by 6-chloropurine. The synthesis of a bicyclic (locked) purine starts from a oxabicycloheptanone with a hydroxymethyl pendant. The preparation
[...] Read more.
The preparation of two nucleoside analogues are reported. Both syntheses involve a key photochemical ring-expansion of cyclobutanones to an oxacarbene and its subsequent scavenging by 6-chloropurine. The synthesis of a bicyclic (locked) purine starts from a oxabicycloheptanone with a hydroxymethyl pendant. The preparation of an isonucleoside uses a cyclobutanone with an α-substituted 6-chloropurine. Irradiation of the latter produces an isonucleoside and acyclic nucleoside analogues. Full article
(This article belongs to the Special Issue Photochemistry in Organic Synthesis)
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Open AccessArticle Probing the Dynamics of Solvation and Structure of the OH- Ion in Aqueous Solution from Picosecond Transient Absorption Measurements
Molecules 2010, 15(5), 3366-3377; doi:10.3390/molecules15053366
Received: 24 March 2010 / Revised: 16 April 2010 / Accepted: 6 May 2010 / Published: 7 May 2010
Cited by 1 | PDF Full-text (413 KB)
Abstract
The reaction of intracomplex proton transfer (44BPY-....HO-H) ® 44BPYH. + OH- that follows the photoreduction of 4,4’-bipyridine (44BPY) into its anion radical 44BPY-in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) is investigated in acetonitrile-water mixtures by using picosecond transient
[...] Read more.
The reaction of intracomplex proton transfer (44BPY-....HO-H) ® 44BPYH. + OH- that follows the photoreduction of 4,4’-bipyridine (44BPY) into its anion radical 44BPY- in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) is investigated in acetonitrile-water mixtures by using picosecond transient absorption. The dependence of the appearance kinetics of the 44BPYH. radical on the water content reveals a highly diffusional proton transfer process that is controlled by the dynamics of solvation of the released hydroxide ion. The results are interpreted on the basis of a two-step mechanism where an intermediate solvation complex (44BPYH.)OH-(H2O)3 is formed first before evolving toward a final four-water hydration structure OH-(H2O)4. Full article
(This article belongs to the Special Issue Photochemistry in Organic Synthesis)
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Open AccessArticle Influence of Solvent, Electron Acceptors and Arenes on Photochemical Decarboxylation of Free Carboxylic Acids via Single Electron Transfer (SET)
Molecules 2010, 15(4), 2623-2630; doi:10.3390/molecules15042623
Received: 15 March 2010 / Revised: 2 April 2010 / Accepted: 7 April 2010 / Published: 12 April 2010
Cited by 19 | PDF Full-text (71 KB)
Abstract
Single electron transfer (SET)-photochemical decarboxylation of free carboxylic acids was performed in a polar solvent using several arenes such as phenanthrene, naphthalene, 1-methylnaphthalene, biphenyl, triphenylene, and chrysene in the presence of various electron acceptors such as 1,2-, 1,3-, and 1,4-dicyanobenzenes, methyl 4-cyanobenzoate, and
[...] Read more.
Single electron transfer (SET)-photochemical decarboxylation of free carboxylic acids was performed in a polar solvent using several arenes such as phenanthrene, naphthalene, 1-methylnaphthalene, biphenyl, triphenylene, and chrysene in the presence of various electron acceptors such as 1,2-, 1,3-, and 1,4-dicyanobenzenes, methyl 4-cyanobenzoate, and 1,4-dicyanonaphthalene. The decarboxylation reaction was influenced by the arenes, electron acceptors, and solvent. The best result was achieved by the photoreaction using biphenyl and 1,4-dicyanonaphthalene in aqueous acetonitrile. Full article
(This article belongs to the Special Issue Photochemistry in Organic Synthesis)
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Review

Jump to: Research

Open AccessReview Photochemistry of Flavonoids
Molecules 2010, 15(8), 5196-5245; doi:10.3390/molecules15085196
Received: 19 May 2010 / Revised: 15 July 2010 / Accepted: 29 July 2010 / Published: 2 August 2010
Cited by 34 | PDF Full-text (461 KB)
Abstract
Flavonoids and their photochemical transformations play an important role in biological processes in nature. Synthetic photochemistry allows access to molecules that cannot be obtained via more conventional methods. This review covers all published synthetic photochemical transformations of the different classes of flavonoids. It
[...] Read more.
Flavonoids and their photochemical transformations play an important role in biological processes in nature. Synthetic photochemistry allows access to molecules that cannot be obtained via more conventional methods. This review covers all published synthetic photochemical transformations of the different classes of flavonoids. It is first comprehensive review on the photochemistry of flavonoids. Full article
(This article belongs to the Special Issue Photochemistry in Organic Synthesis)
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Open AccessReview Photochemical Oxidative Cyclisation of Stilbenes and Stilbenoids—The Mallory-Reaction
Molecules 2010, 15(6), 4334-4358; doi:10.3390/molecules15064334
Received: 2 April 2010 / Revised: 21 May 2010 / Accepted: 9 June 2010 / Published: 14 June 2010
Cited by 76 | PDF Full-text (294 KB)
Abstract
After Mallory described in 1964 the use of iodine as catalyst for the photochemical cyclisation of stilbenes, this reaction has proven its effectiveness in the synthesis of phenanthrenes, other PAHs and phenacenes with a surprisingly large selection of substituents. The “early age” of
[...] Read more.
After Mallory described in 1964 the use of iodine as catalyst for the photochemical cyclisation of stilbenes, this reaction has proven its effectiveness in the synthesis of phenanthrenes, other PAHs and phenacenes with a surprisingly large selection of substituents. The “early age” of the reaction was reviewed by Mallory in 1984in a huge chapter in the Organic Reactions series, but the development has continued. Alternative conditions accommodate more sensitive substituents, and isomers can be favoured by sacrificial substituents. Herein the further developments and applications of this reaction after 1984 are discussed and summarized. Full article
(This article belongs to the Special Issue Photochemistry in Organic Synthesis)
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Open AccessReview Photochemical Transformations of Tetrazole Derivatives: Applications in Organic Synthesis
Molecules 2010, 15(5), 3757-3774; doi:10.3390/molecules15053757
Received: 8 April 2010 / Revised: 1 May 2010 / Accepted: 21 May 2010 / Published: 25 May 2010
Cited by 31 | PDF Full-text (248 KB)
Abstract
Tetrazoles remain a challenge to photochemists. Photolysis leads to cleavage of the tetrazolyl ring, may involve various photodegradation pathways and may produce a diversity of photoproducts, depending on the structure and conformational flexibility of the substituents and the possibility of tautomerism. If the
[...] Read more.
Tetrazoles remain a challenge to photochemists. Photolysis leads to cleavage of the tetrazolyl ring, may involve various photodegradation pathways and may produce a diversity of photoproducts, depending on the structure and conformational flexibility of the substituents and the possibility of tautomerism. If the photochemistry of tetrazoles is considered within the frame of synthetic applications the subject is even more challenging, since the ultimate goal is to achieve selectivity and high yield. In addition, the photoproducts must remain stable and allow isolation or trapping, in order to be used in other reactions. This review summarises the photochemical transformations of tetrazole derivatives that can be used as effective synthetic routes to other compounds. Full article
(This article belongs to the Special Issue Photochemistry in Organic Synthesis)
Open AccessReview Photoresponsive Block Copolymers Containing Azobenzenes and Other Chromophores
Molecules 2010, 15(1), 570-603; doi:10.3390/molecules15010570
Received: 25 December 2009 / Revised: 11 January 2010 / Accepted: 25 January 2010 / Published: 26 January 2010
Cited by 33 | PDF Full-text (3063 KB)
Abstract
Photoresponsive block copolymers (PRBCs) containing azobenzenes and other chromophores can be easily prepared by controlled polymerization. Their photoresponsive behaviors are generally based on photoisomerization, photocrosslinking, photoalignment and photoinduced cooperative motions. When the photoactive block forms mesogenic phases upon microphase separation of PRBCs, supramolecular
[...] Read more.
Photoresponsive block copolymers (PRBCs) containing azobenzenes and other chromophores can be easily prepared by controlled polymerization. Their photoresponsive behaviors are generally based on photoisomerization, photocrosslinking, photoalignment and photoinduced cooperative motions. When the photoactive block forms mesogenic phases upon microphase separation of PRBCs, supramolecular cooperative motion in liquid-crystalline PRBCs enables them to self-organize into hierarchical structures with photoresponsive features. This offers novel opportunities to photocontrol microphase-separated nanostructures of well-defined PRBCs and extends their diverse applications in holograms, nanotemplates, photodeformed devices and microporous films. Full article
(This article belongs to the Special Issue Photochemistry in Organic Synthesis)
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Planned Papers

The below list represents only planned manuscripts. Some of these manuscripts have not been received by the Editorial Office yet. Papers submitted to MDPI journals are subject to peer-review.


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