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Special Issue "Photoactive Molecules"

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

Deadline for manuscript submissions: closed (15 August 2016)

Special Issue Editors

Guest Editor
Prof. Dr. Scott Reed

Department of Chemistry, University of Colorado Denver, Campus Box 194, P.O. Box 173364, Denver, Colorado 80217, USA
Website | E-Mail
Interests: nanoparticle-lipid conjugates as membrane mimics; nanomaterials for phototherapeutic applications; biosensors; aptamers
Guest Editor
Prof. Dr. Marino Resendiz

Department of Chemistry, University of Colorado Denver, Campus Box 194, P.O. Box 173364, Denver, Colorado 80217, USA
Website | E-Mail
Interests: nucleic acid chemistry; RNA; oxidative damage; photochemistry; biosensors; RNA structure; reactive intermediates, miRNA

Special Issue Information

Dear Colleagues,

This special issue of Molecules is focused on studies of photoactive molecules. Contributions that describe any molecular aspects of photochemistry are welcome. We are interested in topics that span organic synthesis, inorganic chemistry, materials science, nanoscale phenomena, and photophysical chemistry. We are interested in articles describing new strategies for the synthesis and assembly of molecules, as well as the use of light to modify surfaces, to effect transformations, and the use of photoactive molecules in sensors and for light harvesting. We encourage authors to submit research papers and comprehensive reviews for this Special Issue. We hope that the submissions will reflect the diverse nature of this field.

Dr. Scott Reed
Dr. Marino Resendiz
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All papers will be peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1800 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • photocatalysts
  • photoinduced electron transfer
  • bioluminescent molecules
  • chemiluminescence
  • fluorescent proteins
  • photodynamic therapy
  • artificial photosynthesis and solar energy
  • photoelectrochemistry
  • supramolecular photochemistry
  • organic and inorganic photochemistry
  • photofunctionalization
  • photoisomerization
  • solid state photochemistry
  • bioorganic photochemistry
  • photochemistry in natural product synthesis
  • photoreversible transformations

Published Papers (8 papers)

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Research

Open AccessArticle Photochemistry of 1,4-Dihydropyridine Derivatives: Diradical Formation, Delocalization and Trapping as a Route to Novel Tricyclic and Tetracyclic Nitrogen Heterocyclic Ring Systems
Molecules 2016, 21(7), 866; doi:10.3390/molecules21070866
Received: 2 June 2016 / Revised: 22 June 2016 / Accepted: 25 June 2016 / Published: 30 June 2016
Cited by 3 | PDF Full-text (2495 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Irradiation of an acetonitrile solution of 4-aryl-3,5-dibenzoyl-1,4-dihydropyridine derivatives 1ac and maleimides 2ac using medium pressure Hg-arc lamp (λ > 290) nm afforded three different cycloadducts 4, 5, 6 in addition to the oxidation products 3. These
[...] Read more.
Irradiation of an acetonitrile solution of 4-aryl-3,5-dibenzoyl-1,4-dihydropyridine derivatives 1ac and maleimides 2ac using medium pressure Hg-arc lamp (λ > 290) nm afforded three different cycloadducts 4, 5, 6 in addition to the oxidation products 3. These results indicate that compounds 1ac undergoes intermolecular cycloaddition reaction through three biradical intermediates and behave photochemically different than those reported previously for the analogous 3,5-diacetyl and 3,5-dicarboxylic acid derivatives. The present work also offers simple access to novel tricyclic and tetracyclic nitrogen heterocyclic ring systems of potential biological and synthetic applications. The structure of the photoproducts was established spectroscopically and by single crystal X-ray crystallography. Full article
(This article belongs to the Special Issue Photoactive Molecules)
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Open AccessArticle A Novel Photosensitizer 31,131-phenylhydrazine -Mppa (BPHM) and Its in Vitro Photodynamic Therapy against HeLa Cells
Molecules 2016, 21(5), 558; doi:10.3390/molecules21050558
Received: 6 February 2016 / Revised: 22 April 2016 / Accepted: 23 April 2016 / Published: 29 April 2016
Cited by 5 | PDF Full-text (4297 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Photodynamic therapy (PDT) has attracted widespread attention due to its potential in the treatment of various cancers. Porphyrinic pyropheophorbide-a (PPa) has been shown to be a potent photosensitizer in PDT experiments. In this paper, a C-31,131 bisphenylhydrazone modified methyl pyropheophorbide-a
[...] Read more.
Photodynamic therapy (PDT) has attracted widespread attention due to its potential in the treatment of various cancers. Porphyrinic pyropheophorbide-a (PPa) has been shown to be a potent photosensitizer in PDT experiments. In this paper, a C-31,131 bisphenylhydrazone modified methyl pyropheophorbide-a (BPHM) was designed and synthesized with the consideration that phenylhydrazone structure may extend absorption wavelength of methyl pyro-pheophorbide-a (Mppa), and make the photosensitizer potential in deep tumor treatment. The synthesis, spectral properties and in vitro photodynamic therapy (PDT) against human HeLa cervical cancer cell line was studied. Methyl thiazolyl tetrazolium (MTT) assay showed the title compound could achieve strong inhibition of cervical cancer cell viability under visible light (675 nm, 25 J/cm2). Cell uptake experiments were performed on HeLa cells. Morphological changes were examined and analyzed by fluorescent inverted microscope. In addition, the mechanism of the photochemical processes of PDT was investigated, which showed that the formation of singlet oxygen after treatment with PDT played a moderate important role. Full article
(This article belongs to the Special Issue Photoactive Molecules)
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Open AccessArticle Conformational and Molecular Structures of α,β-Unsaturated Acrylonitrile Derivatives: Photophysical Properties and Their Frontier Orbitals
Molecules 2016, 21(4), 389; doi:10.3390/molecules21040389
Received: 8 January 2016 / Revised: 10 March 2016 / Accepted: 15 March 2016 / Published: 28 March 2016
PDF Full-text (5851 KB) | HTML Full-text | XML Full-text
Abstract
We report single crystal X-ray diffraction (hereafter, SCXRD) analyses of derivatives featuring the electron-donor N-ethylcarbazole or the (4-diphenylamino)phenyl moieties associated with a -CN group attached to a double bond. The compounds are (2Z)-3-(4-(diphenylamino)-phenyl)-2-(pyridin-3-yl)prop-2-enenitrile (I), (2Z)-3-(4-(diphenylamino)phenyl)-2-(pyridin-4-yl)-prop-2-enenitrile (
[...] Read more.
We report single crystal X-ray diffraction (hereafter, SCXRD) analyses of derivatives featuring the electron-donor N-ethylcarbazole or the (4-diphenylamino)phenyl moieties associated with a -CN group attached to a double bond. The compounds are (2Z)-3-(4-(diphenylamino)-phenyl)-2-(pyridin-3-yl)prop-2-enenitrile (I), (2Z)-3-(4-(diphenylamino)phenyl)-2-(pyridin-4-yl)-prop-2-enenitrile (II) and (2Z)-3-(9-ethyl-9H-carbazol-3-yl)-2-(pyridin-2-yl)enenitrile (III). SCXRD analyses reveal that I and III crystallize in the monoclinic space groups P2/c with Z’ = 2 and C2/c with Z’ = 1, respectively. Compound II crystallized in the orthorhombic space group Pbcn with Z’ = 1. The molecular packing analysis was conducted to examine the pyridine core effect, depending on the ortho, meta- and para-positions of the nitrogen atom, with respect to the optical properties and number of independent molecules (Z’). It is found that the double bond bearing a diphenylamino moiety introduced properties to exhibit a strong π-π-interaction in the solid state. The compounds were examined to evaluate the effects of solvent polarity, the role of the molecular structure, and the molecular interactions on their self-assembly behaviors. Compound I crystallized with a cell with two conformers, anti and syn, due to interaction with solvent. DFT calculations indicated the anti and syn structures of I are energetically stable (less than 1 eV). Also electrochemical and photophysical properties of the compounds were investigated, as well as the determination of optimization calculations in gas and different solvent (chloroform, cyclohexane, methanol, ethanol, tetrahydrofuran, dichloromethane and dimethyl sulfoxide) in the Gaussian09 program. The effect of solvent by PCM method was also investigated. The frontier HOMO and LUMO energies and gap energies are reported. Full article
(This article belongs to the Special Issue Photoactive Molecules)
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Open AccessArticle A Peptoid-Based Fluorescent Sensor for Cyanide Detection
Molecules 2016, 21(3), 339; doi:10.3390/molecules21030339
Received: 22 January 2016 / Revised: 4 March 2016 / Accepted: 7 March 2016 / Published: 10 March 2016
Cited by 5 | PDF Full-text (1658 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
Peptoids, N-substituted glycine oligomers, are versatile peptidomimetics with diverse biomedical applications. However, strategies to the development of novel fluorescent peptoids as chemical sensors have not been extensively explored, yet. Here, we synthesized a novel peptoid-based fluorescent probe in which a coumarin moiety
[...] Read more.
Peptoids, N-substituted glycine oligomers, are versatile peptidomimetics with diverse biomedical applications. However, strategies to the development of novel fluorescent peptoids as chemical sensors have not been extensively explored, yet. Here, we synthesized a novel peptoid-based fluorescent probe in which a coumarin moiety was incorporated via copper(I)-catalyzed azide-alkyne cycloaddition reaction. Fluorescence of the newly generated coumarin-peptoid was dramatically quenched upon coordination of the Cu2+ ion, and the resulting peptoid-Cu2+ complex exhibited significant Turn-ON fluorescence following the addition of CN. The rapid and reversible response, combined with cyanide selectivity of the synthesized peptoid, reflects a multistep photo-process and supports its utility as a new type of CN sensor. Full article
(This article belongs to the Special Issue Photoactive Molecules)
Open AccessArticle Photochemistry of the α-Al2O3-PETN Interface
Molecules 2016, 21(3), 289; doi:10.3390/molecules21030289
Received: 13 January 2016 / Revised: 21 February 2016 / Accepted: 23 February 2016 / Published: 29 February 2016
Cited by 2 | PDF Full-text (4022 KB) | HTML Full-text | XML Full-text
Abstract
Optical absorption measurements are combined with electronic structure calculations to explore photochemistry of an α-Al2O3-PETN interface formed by a nitroester (pentaerythritol tetranitrate, PETN, C5H8N4O12) and a wide band gap aluminum oxide
[...] Read more.
Optical absorption measurements are combined with electronic structure calculations to explore photochemistry of an α-Al2O3-PETN interface formed by a nitroester (pentaerythritol tetranitrate, PETN, C5H8N4O12) and a wide band gap aluminum oxide (α-Al2O3) substrate. The first principles modeling is used to deconstruct and interpret the α-Al2O3-PETN absorption spectrum that has distinct peaks attributed to surface F0-centers and surface—PETN transitions. We predict the low energy α-Al2O3 F0-center—PETN transition, producing the excited triplet state, and α-Al2O3 F0-center—PETN charge transfer, generating the PETN anion radical. This implies that irradiation by commonly used lasers can easily initiate photodecomposition of both excited and charged PETN at the interface. The feasible mechanism of the photodecomposition is proposed. Full article
(This article belongs to the Special Issue Photoactive Molecules)
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Open AccessArticle Synthesis and Characterization of Novel Polythiophenes Containing Pyrene Chromophores: Thermal, Optical and Electrochemical Properties
Molecules 2016, 21(2), 172; doi:10.3390/molecules21020172
Received: 14 December 2015 / Revised: 22 January 2016 / Accepted: 25 January 2016 / Published: 30 January 2016
Cited by 4 | PDF Full-text (4320 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A novel series of pyrene containing thiophene monomers TPM15 were synthesized and fully characterized by FTIR, MS, 1H- and 13C-NMR spectroscopy; their thermal properties were determined by TGA and DSC. These monomers were chemically polymerized using FeCl3 as
[...] Read more.
A novel series of pyrene containing thiophene monomers TPM15 were synthesized and fully characterized by FTIR, MS, 1H- and 13C-NMR spectroscopy; their thermal properties were determined by TGA and DSC. These monomers were chemically polymerized using FeCl3 as oxidizing agent to give the corresponding oligomers TPO15) and they were electrochemically polymerized to obtain the corresponding polymer films deposited onto ITO. All oligomers exhibited good thermal stability, with T10 values between 255 and 299 °C, and Tg values varying from 36 to 39 °C. The monomers showed an absorption band at 345 nm due to the S0 → S2 transition of the pyrene group, whereas the fluorescence spectra showed a broad emission band arising from the “monomer” emission at 375–420 nm. The obtained polymers exhibited two absorption bands at 244 and 354 nm, due to the polythiophene and the pyrene moieties, respectively. The fluorescence spectra of polymers showed a broad “monomer” emission at 380–420 nm followed by an intense excimer emission band at 570 nm, due to the presence of intramolecular pyrene-pyrene interactions in these compounds. Full article
(This article belongs to the Special Issue Photoactive Molecules)
Open AccessArticle An Amidochlorin-Based Colorimetric Fluorescent Probe for Selective Cu2+ Detection
Molecules 2016, 21(1), 107; doi:10.3390/molecules21010107
Received: 5 December 2015 / Revised: 13 January 2016 / Accepted: 14 January 2016 / Published: 18 January 2016
Cited by 6 | PDF Full-text (2423 KB) | HTML Full-text | XML Full-text
Abstract
The design and synthesis of selective and sensitive chemosensors for the quantification of environmentally and biologically important ionic species has attracted widespread attention. Amidochlorin p6 (ACP); an effective colorimetric and fluorescent probe for copper ions (Cu2+) in aqueous solution
[...] Read more.
The design and synthesis of selective and sensitive chemosensors for the quantification of environmentally and biologically important ionic species has attracted widespread attention. Amidochlorin p6 (ACP); an effective colorimetric and fluorescent probe for copper ions (Cu2+) in aqueous solution derived from methyl pheophorbide-a (MPa) was designed and synthesized. A remarkable color change from pale yellow to blue was easily observed by the naked eye upon addition of Cu2+; and a fluorescence quenching was also determined. The research of fluorescent quenching of ACP-Cu2+ complexation showed the detection limit was 7.5 × 10−8 mol/L; which suggested that ACP can act as a high sensitive probe for Cu2+ and can be used to quantitatively detect low levels of Cu2+ in aqueous solution. In aqueous solution the probe exhibits excellent selectivity and sensitivity toward Cu2+ ions over other metal ions (M = Zn2+; Ni2+; Ba2+; Ag+; Co2+; Na+; K+; Mg2+; Cd2+; Pb2+; Mn2+; Fe3+; and Ca2+). The obvious change from pale yellow to blue upon the addition of Cu2+ could make it a suitable “naked eye” indicator for Cu2+. Full article
(This article belongs to the Special Issue Photoactive Molecules)
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Open AccessArticle Solvatochromic and Single Crystal Studies of Two Neutral Triarylmethane Dyes with a Quinone Methide Structure
Molecules 2015, 20(11), 20688-20698; doi:10.3390/molecules201119724
Received: 7 September 2015 / Revised: 30 October 2015 / Accepted: 10 November 2015 / Published: 19 November 2015
Cited by 1 | PDF Full-text (2782 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
The crystal structure of two neutral triarylmethane dyes with a p-quinone methide core was determined by X-ray diffraction analysis. The spectroscopic characteristics of both compounds in 23 solvents with different polarities or hydrogen-bonding donor (HBD) abilities has been studied as a function of
[...] Read more.
The crystal structure of two neutral triarylmethane dyes with a p-quinone methide core was determined by X-ray diffraction analysis. The spectroscopic characteristics of both compounds in 23 solvents with different polarities or hydrogen-bonding donor (HBD) abilities has been studied as a function of three solvatochromic parameters (ET(30), π* and α). Both compounds 1 and 2 showed a pronounced bathochromic shift of the main absorption band on increasing solvent polarity and HBD ability. The correlation is better for compound 2 than for compound 1. The stronger effect and better correlation was observed for compound 2 with the increment of the solvent HBD ability (α parameter). Full article
(This article belongs to the Special Issue Photoactive Molecules)
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