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Synthesis, Characterization and Development of Novel Functional Materials, from Conjugated Polymer to Single Walled Carbon Nanotubes: A Themed Issue Dedicated to Professor Ullrich Scherf

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

Deadline for manuscript submissions: closed (29 February 2024) | Viewed by 15214

Special Issue Editors


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Guest Editor
Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands
Interests: optical and transport properties of organic and hybrid semiconductors; nanomaterials

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Guest Editor
Light Technology Institute, Karlsruhe Institute of Technology (KIT), Engesserstr. 13, 76131 Karlsruhe, Germany
Interests: printed electronics; perovskite optoelectronics; nanostructured devices

Special Issue Information

Dear Colleagues,

The synthesis of novel functional materials is a key step for the development of electronic and optoelectronic devices with unprecedented properties. In particular, in the last few decades, conjugated polymers have emerged as very promising materials able to combine easy deposition, processing, and wide chemical flexibility, typical of polymers, with optoelectronic properties close to the one of inorganic semiconductors.

In some cases, the chemical flexibility and the conformation of these macromolecules are used in surprising ways. An example of these un-orthodox uses is the so-called polymer-wrapping technique that is used nowadays as one of the best ways to select semiconducting single walled nanotubes of narrow chirality distribution.

An enormous contribution to this wide and interesting field has been made through the research of Prof. Ullrich Scherf.

Prof. Dr. Ullrich Scherf graduated in chemistry in 1983 from the Friedrich Schiller University in Jena, Germany, where he obtained his Ph.D. in 1988 on the synthesis of PPV-type organic semiconductors and carbonization of polymer films. In the meantime, he was on a research stay at the Tbilisi State University in 1987.

He then worked for one year Heinz Penzlin at the Institute for Animal Physiology of the Saxonian Academy of Sciences in Leipzig isolating and characterizing cockroach hormones.

From 1990 to 1992 he worked as a scholarship holder of the Chemical Industry Association at the Max Planck Institute for Polymer Research in Mainz under Klaus Müllen, and completed his habilitation in 1996 on polyarylene-type ladder polymers.

From 1992 to 2000 he was Senior Researcher at the Max-Planck-Institute for Polymer Research, Mainz. In 2000 he followed a call to the University of Potsdam, Germany, for a professorship for polymer chemistry. In 2002, he became full professor for Macromolecular Chemistry at Bergische Universitat Wuppertal, Germany. In 2010, he became managing director of the Institute for Polymer Technology at the Bergische Universität.

He has published over 700 refereed papers and he received many awards, like the Meyer-Struckmann Research Award in 1998, the Odysseus Prize in 2010, while in 2011 he was ranked 26th in the global Top 100 Material Scientists ranking by Thomson Reuters.

Molecules is highly pleased to host a Special Issue honoring Prof. Ullrich Scherf for his outstanding achievements in developing a novel functionalized conjugated polymer for different applications, to inspire basic science experiments as well as the development of electronic, optoelectronic and photonic devices based on these materials.

Dr. Marco Anni
Prof. Dr. Maria Antonietta Loi
Prof. Dr. Uli Lemmer
Guest Editors

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Keywords

  • Functional conjugated macromolecules
  • Optoelectronic applications of functional conjugated macromolecules
  • Organic lasers
  • Organic transistors
  • Organic light emitting diodes
  • Carbon nanotubes

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Published Papers (7 papers)

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Research

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16 pages, 3091 KiB  
Article
Effect of Different Substitutions at the 1,7-Bay Positions of Perylenediimide Dyes on Their Optical and Laser Properties
by Nathalie Zink-Lorre, Manuel G. Ramírez, Sara Pla, Pedro G. Boj, José A. Quintana, José M. Villalvilla, Ángela Sastre-Santos, Fernando Fernández-Lázaro and María A. Díaz-García
Molecules 2023, 28(19), 6776; https://doi.org/10.3390/molecules28196776 - 23 Sep 2023
Viewed by 1186
Abstract
Perylenediimide (PDI) compounds are widely used as the active units of thin-film organic lasers. Lately, PDIs bearing two sterically hindering diphenylphenoxy groups at the 1,7-bay positions have received attention because they provide a way to red-shift the emission with respect to bay-unsubstituted PDIs, [...] Read more.
Perylenediimide (PDI) compounds are widely used as the active units of thin-film organic lasers. Lately, PDIs bearing two sterically hindering diphenylphenoxy groups at the 1,7-bay positions have received attention because they provide a way to red-shift the emission with respect to bay-unsubstituted PDIs, while maintaining a good amplified spontaneous emission (ASE) performance at high doping rates. Here, we report the synthesis of a series of six PDI derivatives with different aryloxy groups (PDI 6 to PDI 10) or ethoxy groups (PDI 11) at the 1,7 positions of the PDI core, together with a complete characterization of their optical properties, including absorption, photoluminescence, and ASE. We aim to stablish structure-property relationships that help designing compounds with optimized ASE performance. Film experiments were accomplished at low PDI concentrations in the film, to resemble the isolated molecule behaviour, and at a range of increasing doping rates, to investigate concentration quenching effects. Compounds PDI 10 and PDI 7, bearing substituents in the 2′ positions of the benzene ring (the one contiguous to the linking oxygen atom) attached to the 1,7 positions of the PDI core, have shown a better threshold performance, which is attributed to conformational (steric) effects. Films containing PDI 11 show dual ASE. Full article
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11 pages, 2023 KiB  
Article
Asymmetric AZA-BODIPY with Optical Gain in the Near-Infrared Region
by Tersilla Virgili, Lucia Ganzer, Chiara Botta, Benedetta Maria Squeo and Mariacecilia Pasini
Molecules 2022, 27(14), 4538; https://doi.org/10.3390/molecules27144538 - 15 Jul 2022
Cited by 6 | Viewed by 2011
Abstract
In recent years, there has been a lot of interest in the development of organic compounds emitting in the near-infrared (NIR) region due to their stimulating applications, such as biosensing and light detection and ranging (LiDAR). Moreover, a lot of effort has been [...] Read more.
In recent years, there has been a lot of interest in the development of organic compounds emitting in the near-infrared (NIR) region due to their stimulating applications, such as biosensing and light detection and ranging (LiDAR). Moreover, a lot of effort has been devoted to finding organic emitters with optical gain in the NIR region for lasing applications. In this paper, we present the ultrafast spectroscopy of an asymmetric AZA-BODIPY molecule that shows relevant photophysical changes moving from a diluted solution to a concentrated solution and to a spin-coated film. The diluted solution and the spin-coated film show a bleaching band and a stimulated emission band in the visible region, while the very concentrated solution displays a broad (150 nm) and long-living (more than 400 ps) optical gain band in the NIR region, centered at 900 nm. Our results pave the way for a new organic laser system in a near-infrared spectral region. Full article
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15 pages, 2484 KiB  
Article
Amplified Spontaneous Emission Threshold Dependence on Determination Method in Dye-Doped Polymer and Lead Halide Perovskite Waveguides
by Stefania Milanese, Maria Luisa De Giorgi, Luis Cerdán, Maria-Grazia La-Placa, Nur Fadilah Jamaludin, Annalisa Bruno, Henk J. Bolink, Maksym V. Kovalenko and Marco Anni
Molecules 2022, 27(13), 4261; https://doi.org/10.3390/molecules27134261 - 1 Jul 2022
Cited by 11 | Viewed by 2571
Abstract
Nowadays, the search for novel active materials for laser devices is proceeding faster and faster thanks to the development of innovative materials able to combine excellent stimulated emission properties with low-cost synthesis and processing techniques. In this context, amplified spontaneous emission (ASE) properties [...] Read more.
Nowadays, the search for novel active materials for laser devices is proceeding faster and faster thanks to the development of innovative materials able to combine excellent stimulated emission properties with low-cost synthesis and processing techniques. In this context, amplified spontaneous emission (ASE) properties are typically investigated to characterize the potentiality of a novel material for lasers, and a low ASE threshold is used as the key parameter to select the best candidate. However, several different methods are currently used to define the ASE threshold, hindering meaningful comparisons among various materials. In this work, we quantitatively investigate the ASE threshold dependence on the method used to determine it in thin films of dye-polymer blends and lead halide perovskites. We observe a systematic ASE threshold dependence on the method for all the different tested materials, and demonstrate that the best method choice depends on the kind of information one wants to extract. In particular, the methods that provide the lowest ASE threshold values are able to detect the excitation regime of early-stage ASE, whereas methods that are mostly spread in the literature return higher thresholds, detecting the excitation regime in which ASE becomes the dominant process in the sample emission. Finally, we propose a standard procedure to properly characterize the ASE threshold, in order to allow comparisons between different materials. Full article
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15 pages, 1855 KiB  
Article
Modulated Fluorescence in LB Films Based on DADQs—A Potential Sensing Surface?
by Marek Szablewski, Richard L. Thompson and Lars-Olof Pålsson
Molecules 2022, 27(12), 3893; https://doi.org/10.3390/molecules27123893 - 17 Jun 2022
Cited by 1 | Viewed by 1852
Abstract
Novel fluorescent Langmuir-Blodgett (LB) films have been constructed from three different amphiphilic dicynaoquinodimethanes (DADQs). The DADQs varied in functional group structure, which had an impact on the LB film structure and the fluorescence properties. As the fluorescence of DADQs competes with non-radiative decay [...] Read more.
Novel fluorescent Langmuir-Blodgett (LB) films have been constructed from three different amphiphilic dicynaoquinodimethanes (DADQs). The DADQs varied in functional group structure, which had an impact on the LB film structure and the fluorescence properties. As the fluorescence of DADQs competes with non-radiative decay (conformational change), the packing and/or free volume in the LB film will influence the average fluorescence lifetime and integrated intensity. The pristine (blank) LB films were then exposed to a selection of non-fluorescent target analytes (some with environmental relevance) and the fluorescence was measured and analyzed relative to the pristine LB film. Exposure of the LB films to selected target analytes results in a modulation of the fluorescence, both with respect to average fluorescence lifetime and integrated intensity. The modulation of the fluorescence is different for different DADQ LB films and can be attributed to restricted non-radiative decays or charge transfer reactions between target analyte and DADQ LB film. The response from the DADQ LB films shows that these systems can be developed into sensing surfaces based on fluorescence measurements. Full article
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14 pages, 1227 KiB  
Article
Paper-Based Probes with Visual Response to Vapors from Nitroaromatic Explosives: Polyfluorenes and Tertiary Amines
by Roberto Aguado, A. Rita M. G. Santos, Saúl Vallejos and Artur J. M. Valente
Molecules 2022, 27(9), 2900; https://doi.org/10.3390/molecules27092900 - 2 May 2022
Cited by 9 | Viewed by 1992
Abstract
Although it is well-known that nitroaromatic compounds quench the fluorescence of different conjugated polymers and form colored Meisenheimer complexes with proper nucleophiles, the potential of paper as a substrate for those macromolecules can be further developed. This work undertakes this task, impregnating paper [...] Read more.
Although it is well-known that nitroaromatic compounds quench the fluorescence of different conjugated polymers and form colored Meisenheimer complexes with proper nucleophiles, the potential of paper as a substrate for those macromolecules can be further developed. This work undertakes this task, impregnating paper strips with a fluorene-phenylene copolymer with quaternary ammonium groups, a bisfluorene-based cationic polyelectrolyte, and poly(2-(dimethylamino)ethyl methacrylate) (polyDMAEMA). Cationic groups make the aforementioned polyfluorenes attachable to paper, whose surface possesses a slightly negative charge and avoid interference from cationic quenchers. While conjugated polymers had their fluorescence quenched with nitroaromatic vapors in a non-selective way, polyDMAEMA-coated papers had a visual response that was selective to 2,4,6-trinitrotoluene (TNT), and that could be easily identified, and even quantified, under natural light. Far from implying that polyfluorenes should be ruled out, it must be taken into account that TNT-filled mines emit vapors from 2,4-dinitrotoluene (DNT) and dinitrobenzene isomers, which are more volatile than TNT itself. Atmospheres with only 790 ppbv TNT or 277 ppbv DNT were enough to trigger a distinguishable response, although the requirement for certain exposure times is an important limitation. Full article
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Review

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53 pages, 20673 KiB  
Review
The Double-Cross of Benzotriazole-Based Polymers as Donors and Acceptors in Non-Fullerene Organic Solar Cells
by Laura Crociani
Molecules 2024, 29(15), 3625; https://doi.org/10.3390/molecules29153625 - 31 Jul 2024
Cited by 1 | Viewed by 996
Abstract
Organic solar cells (OSCs) are considered a very promising technology to convert solar energy to electricity and a feasible option for the energy market because of the advantages of light weight, flexibility, and roll-to-roll manufacturing. They are mainly characterized by a bulk heterojunction [...] Read more.
Organic solar cells (OSCs) are considered a very promising technology to convert solar energy to electricity and a feasible option for the energy market because of the advantages of light weight, flexibility, and roll-to-roll manufacturing. They are mainly characterized by a bulk heterojunction structure where a polymer donor is blended with an electron acceptor. Their performance is highly affected by the design of donor–acceptor conjugated polymers and the choice of suitable acceptor. In particular, benzotriazole, a typical electron-deficient penta-heterocycle, has been combined with various donors to provide wide bandgap donor polymers, which have received a great deal of attention with the development of non-fullerene acceptors (NFAs) because of their suitable matching to provide devices with relevant power conversion efficiency (PCE). Moreover, different benzotriazole-based polymers are gaining more and more interest because they are considered promising acceptors in OSCs. Since the development of a suitable method to choose generally a donor/acceptor material is a challenging issue, this review is meant to be useful especially for organic chemical scientists to understand all the progress achieved with benzotriazole-based polymers used as donors with NFAs and as acceptors with different donors in OSCs, in particular referring to the PCE. Full article
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31 pages, 41735 KiB  
Review
Organic Functionalized Carbon Nanostructures for Solar Energy Conversion
by Luca Lazzarin, Mariacecilia Pasini and Enzo Menna
Molecules 2021, 26(17), 5286; https://doi.org/10.3390/molecules26175286 - 31 Aug 2021
Cited by 9 | Viewed by 3121
Abstract
This review presents an overview of the use of organic functionalized carbon nanostructures (CNSs) in solar energy conversion schemes. Our attention was focused in particular on the contribution of organic chemistry to the development of new hybrid materials that find application in dye-sensitized [...] Read more.
This review presents an overview of the use of organic functionalized carbon nanostructures (CNSs) in solar energy conversion schemes. Our attention was focused in particular on the contribution of organic chemistry to the development of new hybrid materials that find application in dye-sensitized solar cells (DSSCs), organic photovoltaics (OPVs), and perovskite solar cells (PSCs), as well as in photocatalytic fuel production, focusing in particular on the most recent literature. The request for new materials able to accompany the green energy transition that are abundant, low-cost, low-toxicity, and made from renewable sources has further increased the interest in CNSs that meet all these requirements. The inclusion of an organic molecule, thanks to both covalent and non-covalent interactions, in a CNS leads to the development of a completely new hybrid material able of combining and improving the properties of both starting materials. In addition to the numerical data, which unequivocally state the positive effect of the new hybrid material, we hope that these examples can inspire further research in the field of photoactive materials from an organic point of view. Full article
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