Special Issue Editor

Prof. Dr. Filip Bureš

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Guest Editor

Faculty of Chemical Technology, Institute of Organic Chemistry and Technology, University of Pardubice, Studentská 573, 53210 Pardubice, Czech Republic
Interests: organic π-conjugated molecules; organic electronics; nonlinear optics; batteries; catalysis; atomic layer deposition

Special Issue Information

Dear Colleagues,

Aromatic compounds comprise a unique and historically well-explored class of organic molecules especially due to their p-conjugated system of electrons and resulting peculiar properties, such as planar arrangement, reactivity, conductivity, color, odor, etc. These properties are even more pronounced by embedding a heteroatom within the aromatic scaffold. The heteroatom may act either as an electron releasing or withdrawing moiety, which allows property fine-tuning along with its chelating and acid/base character. Aromatic heterocycles constitute highly tunable and functionalized organic materials that are very attractive for chemists, physicists, engineers, and materials scientists and represent a burgeoning and long-lasting area of research. They have significantly infiltrated modern organic devices across organic electronics, batteries, switches, sensors, catalysts, drugs, and many others. Hence, this Special Issue covers the synthesis, functionalization, fundamental physicochemical properties, and mostly miscellaneous applications of aromatic heterocyclic compounds.

Prof. Dr. Filip Bureš
Guest Editor

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Keywords

aromatic
heterocycle
organic material
structure–property relationships

Published Papers (3 papers)

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Research

Jump to: Review

12 pages, 2459 KiB

Open AccessArticle

Stimuli-Sensitive Pyrenylated Hydrogels as Optical Sensing Platform for Multiple Metal Ions

by Dipen Biswakarma, Nilanjan Dey and Santanu Bhattacharya

Organics 2023, 4(3), 447-458; https://doi.org/10.3390/org4030032 - 04 Sep 2023

Viewed by 972

Abstract

In the present work, we report a thermoresponsive hydrogel formed by the self-assembly of compounds 1 and 2 Milli Q water. Both hydrogels showed thixotropic behavior. Atomic force microscopy (AFM) studies confirm the fiber-like microstructure of compounds 1 and 2, but denser fibers were observed in the case of compound 1. The hydrogel formed by compound 1 detected Cu²⁺, Fe³⁺, and Hg²⁺, whereas the hydrogel of 2 showed a change in the optical signal, specifically upon adding Cu²⁺ and Hg²⁺. Mechanistically, adding metal ions to the hydrogel resulted in the formation of a (1:1) complex with Fe³⁺ and Hg²⁺ and (2:1) with Cu²⁺. The detection of metal ions has also been achieved in real-life samples, such as in tap water. Low-cost portable gel-coated paper strips have also been developed for the onsite detection of these metal ions. Full article

(This article belongs to the Special Issue Aromatic Heterocycles: A Wonderful Pool of Organic Materials)

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Graphical abstract

5 pages, 518 KiB

Open AccessCommunication

Efficient Synthesis of a 2-Decyl-tetradecyl Substituted 7-Bromophenothiazine-3-carbaldehyde Building Block for Functional Dyes

by Burak Kürsat Börüsah and Thomas J. J. Müller

Organics 2022, 3(4), 502-506; https://doi.org/10.3390/org3040033 - 07 Dec 2022

Cited by 3 | Viewed by 1287

Abstract

(1) Polyfunctional molecules are versatile building blocks for efficient syntheses of novel phenothiazine-based materials with promising electronic properties. A prerequisite is a facile, high yielding access to these building blocks that bear solubilizing moieties and functional groups for orthogonal transformation. (2) Here, an efficient, improved two-step protocol for accessing a solubilizing 2-decyl-tetradecyl functionalized phenothiazine, i.e., an N-alkylated 7-bromophenothiazine-3-carbaldehyde, by Vilsmeier–Haack formylation and NBS (N-bromo succinimide) bromination is reported. (3) The sequence proceeds with higher yields and in shorter reaction times than the standard access employing bromination with elementary bromine. In addition, the work-up procedure essentially uses absorptive filtration on a plug of silica with the eluent. Full article

(This article belongs to the Special Issue Aromatic Heterocycles: A Wonderful Pool of Organic Materials)

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Review

Jump to: Research

24 pages, 5791 KiB

Open AccessReview

Thienothiophene Scaffolds as Building Blocks for (Opto)Electronics

by Jan Podlesný and Filip Bureš

Organics 2022, 3(4), 446-469; https://doi.org/10.3390/org3040029 - 03 Nov 2022

Cited by 3 | Viewed by 1804

Abstract

Thieno[3,2-b]thiophene and isomeric thieno[2,3-b]thiophene represent fused, bicyclic and electron rich heterocycles. These small planar organic compounds belong to the remarkable family of annulated building blocks for various organic materials. The first part of this review focuses on the synthesis of the primary unsubstituted thienothiophene scaffolds. All synthetic pathways available in the literature, dating from the 19th century, are summarized. The second part is devoted to the applications of the thienothiophene-derived materials across (opto)electronics. Organic light emitting diodes, organic solar cells, organic field-effect transistors and nonlinear optics were identified as the most successful application areas of both thienothiophenes. The fundamental structure-property relationships were evaluated for each particular group of derivatives. Full article

(This article belongs to the Special Issue Aromatic Heterocycles: A Wonderful Pool of Organic Materials)

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