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Synthesis, Structure, and Application of Novel Pyrrolic Macrocycles

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

Deadline for manuscript submissions: closed (15 September 2023) | Viewed by 2577

Special Issue Editors


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Guest Editor
School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, China
Interests: porphyrin chemistry;pyrrolic complexes; dyes; pigments; property; application

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Guest Editor
School of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, China
Interests: dyes and pigments; porphyrin chemistry; luminescent materials; property; application

Special Issue Information

Dear Colleagues,

As novel pyrrolic compounds and related π-electron, aromatic systems have expanded their rich applications in the field of organic electronics due to their unique molecular structure, optical and electronic property.

The synthetic methods, structure and catalysis of these novel pyrrolic macrocycles and their complexes are becoming increasingly important in recent years.

The Special Issue entitled "Synthesis, Structure, and Application of Novel Pyrrolic Macrocycles" will provide a platform for researchers to represent new findings and innovative ideas on the advanced synthesis, structure, optical and electronic properties, and applications of novel pyrrolic compounds and their complexes, and nanomaterials, such as MOF and COF.

This Special Issue welcomes the submission of original research papers or comprehensive reviews that demonstrate or summarize significant advances in the novel pyrrolic compounds and their complexes, and nanomaterials, such as MOF and COF, in terms of the synthesis, structures, properties, and application to functional materials.

Dr. Songlin Xue
Prof. Dr. Changjiang Yu
Guest Editors

Manuscript Submission Information

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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

  • porphyrin
  • pyrrolic complexes
  • dyes
  • pigments
  • property
  • application

Published Papers (2 papers)

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Research

11 pages, 3803 KiB  
Article
Facile Synthesis of Asymmetric aza-Boron Dipyrromethene Analogues Bearing Quinoxaline Moiety
by Ru Feng, Zuoxu Chen, Yue Wang, Jianming Pan and Soji Shimizu
Molecules 2023, 28(24), 7940; https://doi.org/10.3390/molecules28247940 - 05 Dec 2023
Viewed by 750
Abstract
An asymmetric aza-BODIPY analogue bearing quinoxaline moiety was synthesized via a titanium tetrachloride-mediated Schiff-base-forming reaction of 6,7-dimethyl-1,4-dihydroquinoxaline-2,3-dione and benzo[d]thiazol-2-amine. This novel aza-BODIPY analogue forms a complementary hydrogen-bonded dimer due to the quinoxaline moiety in the crystal structure. It also shows intense [...] Read more.
An asymmetric aza-BODIPY analogue bearing quinoxaline moiety was synthesized via a titanium tetrachloride-mediated Schiff-base-forming reaction of 6,7-dimethyl-1,4-dihydroquinoxaline-2,3-dione and benzo[d]thiazol-2-amine. This novel aza-BODIPY analogue forms a complementary hydrogen-bonded dimer due to the quinoxaline moiety in the crystal structure. It also shows intense absorption and fluorescence, with fluorescence quantum yields close to unity. The electrochemical measurements and the DFT calculations revealed the presence of the low-lying HOMO, which benefits their potential applications as an electron-transporting material. Full article
(This article belongs to the Special Issue Synthesis, Structure, and Application of Novel Pyrrolic Macrocycles)
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11 pages, 2597 KiB  
Article
Synthesis, Optical Properties, and Fluorescence Cell Imaging of Novel Mixed Fluorinated Subphthalocyanines
by Shutong Zhou, Xiaojuan Lv, Minghui Li, Zijian Gao, Shengnan Tu, Shanshan Qiao, Mengjia Mo, Xu Tang, Yemei Wang and Shasha Sun
Molecules 2023, 28(2), 725; https://doi.org/10.3390/molecules28020725 - 11 Jan 2023
Cited by 2 | Viewed by 1406
Abstract
Subphthalocyanines (SubPcs) are a kind of tripyrrolic macrocycle with a boron atom at their core. Incorporating different units onto the SubPc periphery can endow them with various unique properties. Herein, a series of novel fluorinated low-symmetry SubPc derivatives containing chlorine groups (F8 [...] Read more.
Subphthalocyanines (SubPcs) are a kind of tripyrrolic macrocycle with a boron atom at their core. Incorporating different units onto the SubPc periphery can endow them with various unique properties. Herein, a series of novel fluorinated low-symmetry SubPc derivatives containing chlorine groups (F8-Cl4-SubPc, F4-Cl8-SubPc) and methoxy groups (F8-(OCH3)2-SubPc) were synthesized and characterized by spectral methods (MS, FT-IR, 1H, 13C, 11B, and 19F NMR spectroscopy), and the effect of the peripheral substituents on their electronic structure of low-symmetry macrocycle was investigated by cyclic voltammetry, theoretical calculation, electronic absorption, and emission spectroscopy. In contrast to perfluorinated SubPcs, these low-symmetry SubPcs revealed non-degenerate LUMO and LUMO + 1 orbitals, especially F8-(OCH3)2-SubPc, which was consistent with the split Q-band absorptions. The cyclic voltammetry revealed that these SubPcs exhibited two or three reduction waves and one oxidation wave, which is consistent with the reported SubPcs. Finally, an intracellular fluorescence imaging study of these compounds revealed that these compounds could enter cancer cells and be entrapped in the lysosomes, which provides a possibility of future applications in lysosome fluorescence imaging and targeting. Full article
(This article belongs to the Special Issue Synthesis, Structure, and Application of Novel Pyrrolic Macrocycles)
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