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π-Conjugated Molecular Systems
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π-Conjugated Molecular Systems

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

Deadline for manuscript submissions: closed (28 February 2023) | Viewed by 4271

Special Issue Editor

Prof. Dr. Rajneesh Misra

E-Mail Website
Guest Editor
Department of Chemistry, Indian Institute of Technology Indore, Indore, India
Interests: organic electronics/photonics; supramolecular chemistry; solar cells; OLEDs; organometallic chemistry

Special Issue Information

Dear Colleagues,

In recent years, the design of π-conjugated molecular systems has gained momentum due to their application in energy and health. π-conjugated molecular systems have applications in optoelectronics, supramolecular devices, and biomedical imaging—specifically, organic light-emitting diodes, organic photovoltaics, nonlinear optics, sensing, biomedical imaging, light harvesting for artificial photosynthesis, and many more. This Special Issue is designed to gather scientific papers related to π-conjugated molecular systems.

Prof. Dr. Rajneesh Misra
Guest Editor

Manuscript Submission Information

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Keywords

  • photophysics
  • donor–acceptor
  • Pi-conjugation
  • sensing
  • charge transfer
  • organometallics

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Published Papers (2 papers)

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Research

19 pages, 6047 KiB  
Article
Pyrene-Fused Poly-Aromatic Regioisomers: Synthesis, Columnar Mesomorphism, and Optical Properties
by Qing Zeng, Shuai Liu, Hang Lin, Ke-Xiao Zhao, Xiao-Yan Bai, Ke-Qing Zhao, Ping Hu, Bi-Qin Wang and Bertrand Donnio
Molecules 2023, 28(4), 1721; https://doi.org/10.3390/molecules28041721 - 10 Feb 2023
Cited by 9 | Viewed by 2233
Abstract
π-Extended pyrene compounds possess remarkable luminescent and semiconducting properties and are being intensively investigated as electroluminescent materials for potential uses in organic light-emitting diodes, transistors, and solar cells. Here, the synthesis of two sets of pyrene-containing π-conjugated polyaromatic regioisomers, namely 2,3,10,11,14,15,20,21-octaalkyloxypentabenzo[a, [...] Read more.
π-Extended pyrene compounds possess remarkable luminescent and semiconducting properties and are being intensively investigated as electroluminescent materials for potential uses in organic light-emitting diodes, transistors, and solar cells. Here, the synthesis of two sets of pyrene-containing π-conjugated polyaromatic regioisomers, namely 2,3,10,11,14,15,20,21-octaalkyloxypentabenzo[a,c,m,o,rst]pentaphene (BBPn) and 2,3,6,7,13,14,17,18-octaalkyloxydibenzo[j,tuv]phenanthro [9,10-b]picene (DBPn), is reported. They were obtained using the Suzuki–Miyaura cross-coupling in tandem with Scholl oxidative cyclodehydrogenation reactions from the easily accessible precursors 1,8- and 1,6-dibromopyrene, respectively. Both sets of compounds, equipped with eight peripheral aliphatic chains, self-assemble into a single hexagonal columnar mesophase, with one short-chain BBPn homolog also exhibiting another columnar mesophase at a lower temperature, with a rectangular symmetry; BBPn isomers also possess wider mesophase ranges and higher mesophases’ stability than their DBPn homologs. These polycyclic aromatic hydrocarbons all show a strong tendency of face-on orientation on the substrate and could be controlled to edge-on alignment through mechanical shearing of interest for their implementation in photoelectronic devices. In addition, both series BBPn and DBPn display green-yellow luminescence, with high fluorescence quantum yields, around 30%. In particular, BBPn exhibit a blue shift phenomenon in both absorption and emission with respect to their DBPn isomers. DFT results were in good agreement with the optical properties and with the stability ranges of the mesophases by confirming the higher divergence from the flatness of DBPn compared with BBPn. Based on these interesting properties, these isomers could be potentially applied not only in the field of fluorescent dyes but also in the field of organic photoelectric semiconductor materials as electron transport materials. Full article
(This article belongs to the Special Issue π-Conjugated Molecular Systems)
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17 pages, 4962 KiB  
Article
Manipulating the Subcellular Localization and Anticancer Effects of Benzophenothiaziniums by Minor Alterations of N-Alkylation
by Yanping Wu, Yuncong Chen, Shankun Yao, Shumeng Li, Hao Yuan, Fen Qi, Weijiang He and Zijian Guo
Molecules 2023, 28(4), 1714; https://doi.org/10.3390/molecules28041714 - 10 Feb 2023
Cited by 1 | Viewed by 1706
Abstract
Cationic, water-soluble benzophenothiaziniums have been recognized as effective type I photosensitizers (PSs) against hypoxic tumor cells. However, the study of the structure–property relationship of this type of PS is still worth further exploration to achieve optimized photodynamic effects and minimize the potential side [...] Read more.
Cationic, water-soluble benzophenothiaziniums have been recognized as effective type I photosensitizers (PSs) against hypoxic tumor cells. However, the study of the structure–property relationship of this type of PS is still worth further exploration to achieve optimized photodynamic effects and minimize the potential side effects. Herein, we synthesized a series of benzophenothiazine derivatives with minor N-alkyl alteration to study the effects on the structure–property relationships. The cellular uptake, subcellular organelle localization, reactive oxygen species (ROS) generation, and photocytotoxicity performances were systematically investigated. NH2NBS and EtNBS specifically localized in lysosomes and exhibited high toxicity under light with a moderate phototoxicity index (PI) due to the undesirable dark toxicity. However, NMe2NBS with two methyl substitutions accumulated more in mitochondria and displayed an excellent PI value with moderate light toxicity and negligible dark toxicity. Without light irradiation, NH2NBS and EtNBS could induce lysosomal membrane permeabilization (LMP), while NMe2NBS showed no obvious damage to lysosomes. After irradiation, NH2NBS and EtNBS were released from lysosomes and relocated into mitochondria. All compounds could induce mitochondria membrane potential (MMP) loss and nicotinamide adenine dinucleotide phosphate (NADPH) consumption under light to cause cell death. NMe2NBS exhibited remarkable in vivo photodynamic therapy (PDT) efficacy in a xenograft mouse tumor (inhibition rate, 89%) with no obvious side effects. This work provides a valuable methodology to investigate the structure–property relationships of benzophenothiazine dyes, which is of great importance in the practical application of PDT against hypoxia tumor cells. Full article
(This article belongs to the Special Issue π-Conjugated Molecular Systems)
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