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Molecules
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Photochemical Reaction of Aromatic Compounds - Something Old, Something New
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Photochemical Reaction of Aromatic Compounds - Something Old, Something New

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

Deadline for manuscript submissions: closed (31 July 2022) | Viewed by 8430

Special Issue Editor

Prof. Dr. Vladimir Khodorkovsky

E-Mail Website1 Website2
Guest Editor
Aix Marseille Université, CNRS, CINaM UMR 7325, Marseille, France
Interests: photochemistry; charge and electron transfer; quantum mechanical calculations

Special Issue Information

Dear Colleagues,

The photochemistry of organic molecules is an early field of organic chemistry originating from the first observation of a sunlight-induced chemical reaction in 1834. The mechanism of this reaction was only established in 2007. The advent of new light sources revolutionized this field, although utilizing sunlight related to energy harvesting and storage is still a major research focus. Irreversible and reversible photochemical reactions can be employed, in particular, for the synthesis of compounds that are difficult to prepare by traditional synthetic approaches—photopolymerization, photochemical acid generation and photopharmacology, information storage, and other applications. Aromatic compounds are of particular interest among the known types of photoactive molecules, owing to their intrinsic electronic structure (photoinduced acquiring/loss of aromaticity), or in combination with various substituents at the aromatic ring. This Special Issue will involve original reports and reviews dealing with irreversible and reversible (including photochromic) light-induced reactions of known or newly designed aromatic compounds.

Prof. Dr. Vladimir Khodorkovsky
Guest Editor

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 submissions that pass pre-check are 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 semimonthly 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 2700 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

  • preparative photochemistry
  • computational photochemistry
  • photochromism
  • photoswitches
  • photoenolization
  • photocatalysis
  • photopolymerization
  • aromatic compounds

Published Papers (2 papers)

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Research

15 pages, 13780 KiB  
Article
Synthesis of Cyclic Peptides in SPPS with Npb-OH Photolabile Protecting Group
by Tingting Chen, Gang Wang, Lin Tang, Hongpeng Yang, Jing Xu, Xiaoxue Wen, Yunbo Sun, Shuchen Liu, Tao Peng, Shouguo Zhang and Lin Wang
Molecules 2022, 27(7), 2231; https://doi.org/10.3390/molecules27072231 - 29 Mar 2022
Viewed by 2116
Abstract
Significant efforts have been made in recent years to identify more environmentally benign and safe alternatives to side-chain protection and deprotection in solid-phase peptide synthesis (SPPS). Several protecting groups have been endorsed as suitable candidates, but finding a greener protecting group in SPPS [...] Read more.
Significant efforts have been made in recent years to identify more environmentally benign and safe alternatives to side-chain protection and deprotection in solid-phase peptide synthesis (SPPS). Several protecting groups have been endorsed as suitable candidates, but finding a greener protecting group in SPPS has been challenging. Here, based on the 2-(o-nitrophenyl) propan-1-ol (Npp-OH) photolabile protecting group, a structural modification was carried out to synthesize a series of derivatives. Through experimental verification, we found that 3-(o-Nitrophenyl) butan-2-ol (Npb-OH) had a high photo-release rate, high tolerance to the key conditions of Fmoc-SPPS (20% piperidine DMF alkaline solution, and pure TFA acidic solution), and applicability as a carboxyl-protective group in aliphatic and aromatic carboxyl groups. Finally, Npb-OH was successfully applied to the synthesis of head–tail cyclic peptides and side-chain–tail cyclic peptides. Moreover, we found that Npb-OH could effectively resist diketopiperazines (DKP). The α-H of Npb-OH was found to be necessary for its photosensitivity in comparison to 3-(o-Nitrophenyl)but-3-en-2-ol (Npbe-OH) during photolysis-rate verification. Full article
(This article belongs to the Special Issue Photochemical Reaction of Aromatic Compounds - Something Old, Something New)
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9 pages, 2569 KiB  
Article
Light-Induced Reactions within Poly(4-vinyl pyridine)/Pyridine Gels: The 1,6-Polyazaacetylene Oligomers Formation
by Evgenia Vaganova, Dror Eliaz, Ulyana Shimanovich, Gregory Leitus, Emad Aqad, Vladimir Lokshin and Vladimir Khodorkovsky
Molecules 2021, 26(22), 6925; https://doi.org/10.3390/molecules26226925 - 17 Nov 2021
Cited by 4 | Viewed by 5544
Abstract
Cyclic 6-membered aromatic compounds such as benzene and azabenzenes (pyridine, pyridazine, and pyrazine) are known to be light-sensitive, affording, in particular, the Dewar benzene type of intermediates. Pyridine is known to provide the only Dewar pyridine intermediate that undergoes reversible ring-opening. We found [...] Read more.
Cyclic 6-membered aromatic compounds such as benzene and azabenzenes (pyridine, pyridazine, and pyrazine) are known to be light-sensitive, affording, in particular, the Dewar benzene type of intermediates. Pyridine is known to provide the only Dewar pyridine intermediate that undergoes reversible ring-opening. We found that irradiation of photosensitive gels prepared from poly(4-vinyl pyridine) and pyridine at 254 or 312 nm leads to pyridine ring-opening and subsequent formation of 5-amino-2,4-pentadienals. We show that this light-induced process is only partially reversible, and that the photogenerated aminoaldehyde and aminoaldehyde-pending groups undergo self-condensation to produce cross-linked, conjugated oligomers that absorb light in the visible spectrum up to the near-infrared range. Such a sequence of chemical reactions results in the formation of gel with two distinct morphologies: spheres and fiber-like matrices. To gain deeper insight into this process, we prepared poly(4-vinyl pyridine) with low molecular weight (about 2000 g/mol) and monitored the respective changes in absorption, fluorescence, 1H-NMR spectra, and electrical conductivity. The conductivity of the polymer gel upon irradiation changes from ionic to electronic, indicative of a conjugated molecular wire behavior. Quantum mechanical calculations confirmed the feasibility of the proposed polycondensation process. This new polyacetylene analog has potential in thermal energy-harvesting and sensor applications. Full article
(This article belongs to the Special Issue Photochemical Reaction of Aromatic Compounds - Something Old, Something New)
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