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

Deadline for manuscript submissions: 31 December 2024 | Viewed by 15720

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Special Issue Editors

Prof. Dr. Shiyong Liu

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Faculty of Materials Metallurgy and Chemistry, Jiangxi University of Science and Technology, Ganzhou 341000, China
Interests: π-functional materials; step and atom economic synthesis; direct C-H arylation; conjugated porous polymers; organic electronics; organic photovoltaics; photocatalysis; photocatalytic water splitting

Dr. Guangfu Liao

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Guest Editor

College of Material Engineering, Fujian Agriculture and Forestry University, Fuzhou 350002, China
Interests: photo- and electrocatalysis; polymer synthesis and applications; polymer membranes; redox flow batteries; nanoporous and nanostructured materials; biomaterials; gas storage and energy conversion
Special Issues, Collections and Topics in MDPI journals

Dr. Jiabin Qiu

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Faculty of Materials Metallurgy and Chemistry, Jiangxi University of Science and Technology, Ganzhou 341000, China
Interests: π-functional materials; direct C-H arylation; p-conjugated polymers; organic electronics; organic photovoltaics; photocatalysis; photocatalytic water splitting; diphenylacrylonitrile; aggregation-induced emission (AIE); fluorescent probe

Special Issue Information

Dear Colleagues,

π-conjugated functional molecules and polymers, as the fundamental building blocks for organic optoelectronics, have found wide-ranging applications in optics, electronics and renewable energies, such as aggregation-induced emissions (AIEs), nonlinear optics (NLOs), organic light-emitting diodes (OLEDs), organic field effect transistors (OFETs), organic photovoltaic cells (OPVs), photocatalysis, etc. The development of new and high-performance π-functional materials is critical to push the above technologies into practical applications. Moreover, the efficient synthesis of and knowledge on structure–property–performance correlations are crucial for the development and optimization of new π-functional materials. This Special Issue aims to gather papers on the latest advances in this field from a materials chemistry point of view from across the scientific community. Key aspects, such as molecular design, synthesis, optoelectronic properties and the performance of the any π-functional material, including conjugated molecules and polymers, covalent organic framework, MOF and conjugated porous polymers, will be considered in this Special Issue.

Prof. Dr. Shiyong Liu
Dr. Guangfu Liao
Dr. Jiabin Qiu
Guest Editors

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Keywords

π-conjugated functional materials
conjugated porous polymers
covalent organic framework
metal–organic framework
synthetic methodology
aggregation-induced organic emissions
nonlinear optics
light-emitting diodes
organic field effect transistors
organic photovoltaic cells
photocatalysis

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Published Papers (12 papers)

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Research

19 pages, 6287 KiB

Open AccessArticle

Investigating Excited States and Absorption Spectra of the Poly-cyclopenta-dithiophene-benzothiadiazole Oligomers (Poly-CPDTBT)—A Theoretical Study

by Jun Wang, Yuting Huang, Yajing Wang, Bo Durbeej and Lluís Blancafort

Molecules 2024, 29(22), 5348; https://doi.org/10.3390/molecules29225348 - 14 Nov 2024

Viewed by 707

Abstract

Poly-CPDTBT, as typical low-band gap copolymers, have potential applications in organic bulk heterojunction solar cells. To have a clear picture of its excited-state processes, the first task is to understand their excited states, in particular, electronic character and relevant optical absorption. Herein, the low-lying singlet excited states of Poly-CPDTBT oligomers were investigated via Algebraic Diagrammatic Construction Second Order (ADC(2)) and time-dependent density functional theory (TDDFT) method with several functionals. Six CPDTBT_N (N = 1–6) oligomers were taken as prototypes to study their excited states in detail. The results provide interesting clues to extrapolate the photophysical properties of such polymers with potential applications in photovoltaic materials. The result provided by ωB97XD functional gives good agreement with the experiment result. The vertical excitation energies of the four lowest excited states decrease almost linearly with increasing polymerization degree (N) for CPDTBT_N (N = 1–6). The transition density analysis indicates that the local excitations (LE) and the short-distance charge transfer (CT) excitations between two adjacent CPDT and BT units are dominant for low-lying excited states for short oligomers. For the long-chain oligomers (trimer to hexamer), the transition density shows a ladder (or zigzag) pattern along the diagonal blocks at the planar geometry. For long oligomers, the whole chain is involved in the transitions, and the CT excitations only exist between two adjacent CPDT and BT units. The present work provides a valuable basis for understanding the excited-state processes of Poly-CPDTBT and other conjugated polymers that conduct solar energy conversions, which has great significance for the development of new solar cells. Full article

(This article belongs to the Special Issue π-Conjugated Functional Molecules & Polymers)

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10 pages, 2326 KiB

Open AccessCommunication

Conjugated Diphenylaniline-Azulene Co-Oligomers with Intense Absorption and Emission in the Visible Region

by Nurlan Merkhatuly, Amantay Iskanderov, Saltanat Abeuova, Ablaykhan Iskanderov and Saltanat Zhokizhanova

Molecules 2024, 29(21), 5041; https://doi.org/10.3390/molecules29215041 - 25 Oct 2024

Viewed by 517

Abstract

New conjugated 2,6-diphenylaniline-azulene co-oligomers of linear and branched structure were synthesized by the interaction of borylazulenes with diphenylaniline bromides under Suzuki–Miyaura cross-coupling conditions. The obtained diphenylaniline-azulene co-oligomers intensively absorb and emit visible light (410–700 nm region); in particular, they exhibit strong emissions in the green, as well as orange, range, with maxima of 510/590 nm. It is shown that such properties appear as a result of the positive resonance exposure to aniline fragments significantly rearranging the electronic structure of azulene, in particular, the levels and energy gaps of frontal HOMO–LUMO orbitals. Full article

(This article belongs to the Special Issue π-Conjugated Functional Molecules & Polymers)

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16 pages, 2800 KiB

Open AccessArticle

Enhancement and Compatibilization of Waste-Sourced Biocomposites Through Elastomer Blending and Matrix Grafting Modification

by Shunmin Yi, Wanyu Liu, Shihua Xu, Ruijia Hu, Qing Li, Meijia Wu, Qingwen Wang and Zhimin Huang

Molecules 2024, 29(20), 4905; https://doi.org/10.3390/molecules29204905 - 16 Oct 2024

Viewed by 509

Abstract

A novel elastomer-modified multicomponent, multiphase waste-sourced biocomposites, was prepared for converting waste biomass and plastic into value-added products. The effects of blending elastomer–olefin block copolymer (OBC) and maleic anhydride (MAH), and divinylbenzene (DVB) co-grafting of recycled polypropylene (rPP) matrix on the adhesion interface, structure, and properties of high wood flour-filled (60 wt.%) composites were thoroughly investigated. The results indicated that DVB introduced branched structures into the polymer matrix molecular chain and increased the MAH grafting rate. Co-grafting rPP/OBC blends enhanced the interfacial adhesion among rPP, OBC, and wood flour. Additionally, MAH-grafted OBC was prone to encapsulating rigid wood flour, thereby forming an embedded structure. Notably, the tensile modulus and impact strength of the final three-component composites increased by 60% and 125%, respectively, compared with the unmodified composites. Additionally, dynamic mechanical analysis revealed that DVB-induced branching promoted the formation of microvoids in the OBC shell layer surrounding the wood, which in turn induced significant plastic deformation in the polymer matrix. This work offers a facile and efficient method for preparing high-toughness, high-stiffness, and low-cost waste PP-based composites for automotive interiors, and indoor and outdoor decoration. Full article

(This article belongs to the Special Issue π-Conjugated Functional Molecules & Polymers)

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13 pages, 2497 KiB

Open AccessArticle

Impact of Different π-Bridges on the Photovoltaic Performance of A-D-D′-D-A Small Molecule-Based Donors

by Lingjun Yang, Yu Wu, Pachaiyappan Murugan, Peng Liu, Yulong Peng, Zhiyong Qiu, Zaifang Li, Changlin Yu and Shiyong Liu

Molecules 2024, 29(17), 4231; https://doi.org/10.3390/molecules29174231 - 6 Sep 2024

Viewed by 642

Abstract

Three small donor molecule materials (S1, S2, S3) based on dithiophene [2,3-d:2′,3′-d′]dithiophene [1,2-b:4,5-b′]dithiophene (DTBDT) utilized in this study were synthesized using the Vilsmeier–Haack reaction, traditional Stille coupling, and Knoevenagel condensation. Then, a variety of characterization methods were applied to study the differences in optical properties and photovoltaic devices among the three. By synthesizing S2 using a thiophene π-bridge based on S1, the blue shift in ultraviolet absorption can be enhanced, the band gap and energy level can be reduced, the open circuit voltage (V_OC) can be increased to 0.75 V using the S2:Y6 device, and a power conversion efficiency (PCE) of 3% can be achieved. Also, after developing the device using Y6, S3 introduced the alkyl chain of thiophene π-bridge to S2, which improved the solubility of tiny donor molecules, achieved the maximum short-circuit current (J_SC = 10.59 mA/cm²), filling factor (FF = 49.72%), and PCE (4.25%). Thus, a viable option for future design and synthesis of small donor molecule materials is to incorporate thiophene π-bridges into these materials, along with alkyl chains, in order to enhance the device’s morphology and charge transfer behavior. Full article

(This article belongs to the Special Issue π-Conjugated Functional Molecules & Polymers)

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10 pages, 1883 KiB

Open AccessCommunication

Introduction of Electron Donor Groups into the Azulene Structure: The Appearance of Intense Absorption and Emission in the Visible Region

by Nurlan Merkhatuly, Ablaykhan Iskanderov, Saltanat Abeuova, Amantay Iskanderov and Saltanat Zhokizhanova

Molecules 2024, 29(14), 3354; https://doi.org/10.3390/molecules29143354 - 17 Jul 2024

Viewed by 950

Abstract

In this work, through the Suzuki–Miyaura cross-coupling reaction with high yields, new π-conjugated azulene compounds containing diphenylaniline groups at positions 2 and 6 of azulene were synthesized. The obtained diphenylaniline–azulenes have intensely visible-light absorbing and emitting (in the wavelength range from 400 to 600 nm) properties. It has been shown that such unique optical properties, in particular fluorescent emission in the region of blue and green photoluminescence (λem at 495 and 525 nm), which were absent in the original azulene, are the result of the electron donor effect of diphenylaniline groups, which significantly changes the electronic structure of azulene and leads to the allowed HOMO → LUMO electron transition. Full article

(This article belongs to the Special Issue π-Conjugated Functional Molecules & Polymers)

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11 pages, 2026 KiB

Open AccessArticle

Doping Ferrocene-Based Conjugated Microporous Polymers with 7,7,8,8-Tetracyanoquinodimethane for Efficient Photocatalytic CO₂ Reduction

by Shenglin Wang, Qianqian Yan, Hui Hu, Xiaofang Su, Huanjun Xu, Jianyi Wang and Yanan Gao

Molecules 2024, 29(8), 1738; https://doi.org/10.3390/molecules29081738 - 11 Apr 2024

Viewed by 1184

Abstract

The design and synthesis of organic photocatalysts remain a great challenge due to their strict structural constraints. However, this could be mitigated by achieving structural flexibility by constructing permanent porosity into the materials. Conjugated microporous polymers (CMPs) are an emerging class of porous materials with an amorphous, three-dimensional network structure, which makes it possible to integrate the elaborate functional groups to enhance photocatalytic performance. Here, we report the synthesis of a novel CMP, named TAPFc-TFPPy-CMP, constructed by 1,1′3,3′-tetra(4-aminophenyl)ferrocene (TAPFc) and 1,3,6,8-tetrakis(4-formylphenyl)pyrene (TFPPy) monomers. The integration of the p-type dopant 7,7,8,8-tetracyanoquinodimethane (TCNQ) into the TAPFc-TFPPy-CMP improved the light adsorption performance, leading to a decrease in the optical bandgap from 2.00 to 1.43 eV. The doped CMP (TCNQ@TAPFc-TFPPy-CMP) exhibited promising catalytic activity in photocatalytic CO₂ reduction under visible light, yielding 546.8 μmol g⁻¹ h⁻¹ of CO with a selectivity of 96% and 5.2 μmol g⁻¹ h⁻¹ of CH₄. This represented an 80% increase in the CO yield compared to the maternal TAPFc-TFPPy-CMP. The steady-state photoluminescence (PL) and fluorescence lifetime (FL) measurements reveal faster carrier separation and transport after the doping. This study provides guidance for the development of organic photocatalysts for the utilization of renewable energy. Full article

(This article belongs to the Special Issue π-Conjugated Functional Molecules & Polymers)

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14 pages, 4512 KiB

Open AccessArticle

Functionalized Linear Conjugated Polymer/TiO₂ Heterojunctions for Significantly Enhancing Photocatalytic H₂ Evolution

by Hao Gong, Yuqin Xing, Jinhua Li and Shiyong Liu

Molecules 2024, 29(5), 1103; https://doi.org/10.3390/molecules29051103 - 29 Feb 2024

Cited by 1 | Viewed by 1306

Abstract

Conjugated polymers (CPs) have attracted much attention in recent years due to their structural abundance and tunable energy bands. Compared with CP-based materials, the inorganic semiconductor TiO₂ has the advantages of low cost, non-toxicity and high photocatalytic hydrogen production (PHP) performance. However, studies on polymeric-inorganic heterojunctions, composed of D-A type CPs and TiO₂, for boosting the PHP efficiency are still rare. Herein, an elucidation that the photocatalytic hydrogen evolution activity can actually be improved by forming polymeric-inorganic heterojunctions TFl@TiO₂, TS@TiO₂ and TSO₂@TiO₂, facilely synthesized through efficient in situ direct C–H arylation polymerization, is given. The compatible energy levels between virgin TiO₂ and polymeric semiconductors enable the resulting functionalized CP@TiO₂ heterojunctions to exhibit a considerable photocatalytic hydrogen evolution rate (HER). Especially, the HER of TSO₂@TiO₂ heterojunction reaches up to 11,220 μmol g⁻¹ h⁻¹, approximately 5.47 and 1260 times higher than that of pristine TSO₂ and TiO₂ photocatalysts. The intrinsic merits of a donor-acceptor conjugated polymer and the interfacial interaction between CP and TiO₂ account for the excellent PHP activity, facilitating the separation of photo-generated excitons. Considering the outstanding PHP behavior, our work discloses that the coupling of inorganic semiconductors and suitable D-A conjugated CPs would play significant roles in the photocatalysis community. Full article

(This article belongs to the Special Issue π-Conjugated Functional Molecules & Polymers)

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12 pages, 4626 KiB

Open AccessArticle

Organic Transistors Based on Highly Crystalline Donor–Acceptor π-Conjugated Polymer of Pentathiophene and Diketopyrrolopyrrole

by Shiwei Ren, Zhuoer Wang, Jinyang Chen, Sichun Wang and Zhengran Yi

Molecules 2024, 29(2), 457; https://doi.org/10.3390/molecules29020457 - 17 Jan 2024

Cited by 2 | Viewed by 1492

Abstract

Oligomers and polymers consisting of multiple thiophenes are widely used in organic electronics such as organic transistors and sensors because of their strong electron-donating ability. In this study, a solution to the problem of the poor solubility of polythiophene systems was developed. A novel π-conjugated polymer material, PDPP-5Th, was synthesized by adding the electron acceptor unit, DPP, to the polythiophene system with a long alkyl side chain, which facilitated the solution processing of the material for the preparation of devices. Meanwhile, the presence of the multicarbonyl groups within the DPP molecule facilitated donor–acceptor interactions in the internal chain, which further improved the hole-transport properties of the polythiophene-based material. The weak forces present within the molecules that promoted structural coplanarity were analyzed using theoretical simulations. Furthermore, the grazing incidence wide-angle X-ray scanning (GIWAXS) results indicated that PDPP-5Th features high crystallinity, which is favorable for efficient carrier migration within and between polymer chains. The material showed hole transport properties as high as 0.44 cm² V⁻¹ s⁻¹ in conductivity testing. Our investigations demonstrate the great potential of this polymer material in the field of optoelectronics. Full article

(This article belongs to the Special Issue π-Conjugated Functional Molecules & Polymers)

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10 pages, 3622 KiB

Open AccessCommunication

Incorporation of Diketopyrrolopyrrole into Polythiophene for the Preparation of Organic Polymer Transistors

by Shiwei Ren, Zhuoer Wang, Wenqing Zhang, Abderrahim Yassar, Jinyang Chen and Sichun Wang

Molecules 2024, 29(1), 260; https://doi.org/10.3390/molecules29010260 - 3 Jan 2024

Cited by 4 | Viewed by 1462

Abstract

Polythiophene, as a class of potential electron donor units, is widely used in organic electronics such as transistors. In this work, a novel polymeric material, PDPPTT-FT, was prepared by incorporating the electron acceptor unit into the polythiophene system. The incorporation of the DPP molecule assists in improving the solubility of the material and provides a convenient method for the preparation of field effect transistors via subsequent solution processing. The introduction of fluorine atoms forms a good intramolecular conformational lock, and theoretical calculations show that the structure displays excellent co-planarity and regularity. Grazing incidence wide-angle X-ray (GIWAXS) results indicate that the PDPPTT-FT is highly crystalline, which facilitates carrier migration within and between polymer chains. The hole mobility of this π-conjugated material is as high as 0.30 cm² V⁻¹ s⁻¹ in organic transistor measurements, demonstrating the great potential of this polymer material in the field of optoelectronics. Full article

(This article belongs to the Special Issue π-Conjugated Functional Molecules & Polymers)

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13 pages, 1729 KiB

Open AccessArticle

Systematic Assessment of the Catalytic Reactivity of Frustrated Lewis Pairs in C-H Bond Activation

by Yongjie Guo, Xueqi Lian, Hao Zhang, Xueling Zhang, Jun Chen, Changzhong Chen, Xiaobing Lan and Youxiang Shao

Molecules 2024, 29(1), 24; https://doi.org/10.3390/molecules29010024 - 19 Dec 2023

Viewed by 1450

Abstract

Unreactive C-H bond activation is a new horizon for frustrated Lewis pair (FLP) chemistry. This study provides a systematic assessment of the catalytic reactivity of recently reported intra-molecular FLPs on the activation of typical inert C-H bonds, including 1-methylpyrrole, methane, benzyl, propylene, and benzene, in terms of density functional theory (DFT) calculations. The reactivity of FLPs is evaluated according to the calculated reaction thermodynamic and energy barriers of C-H bond activation processes in the framework of concerted C-H activation mechanisms. As for 1-methylpyrrole, 14 types of N-B-based and 15 types of P-B-based FLPs are proposed to be active. Although none of the evaluated FLPs are able to catalyze the C-H activation of methane, benzyl, or propylene, four types of N-B-based FLPs are suggested to be capable of catalyzing the activation of benzene. Moreover, the influence of the strength of Lewis acid (LA) and Lewis base (LB), and the differences between the influences of LA and LB on the catalytic reactivity of FLPs, are also discussed briefly. This systematic assessment of the catalytic activity of FLPs should provide valuable guidelines to aid the development of efficient FLP-based metal-free catalysts for C-H bond activation. Full article

(This article belongs to the Special Issue π-Conjugated Functional Molecules & Polymers)

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12 pages, 1241 KiB

Open AccessCommunication

A Simple and Practical Bis-N-Heterocyclic Carbene as an Efficient Ligand in Cu-Catalyzed Glaser Reaction

by Jie Liu, Yao Zhu, Jun Luo, Ziyi Zhu, Lin Zhao, Xiaoyan Zeng, Dongdong Li, Jun Chen and Xiaobing Lan

Molecules 2023, 28(13), 5083; https://doi.org/10.3390/molecules28135083 - 29 Jun 2023

Cited by 2 | Viewed by 1717

Abstract

Conjugated diyne derivatives are important scaffolds in modern organic synthetic chemistry. Using the Glaser reaction involves the coupling of terminal alkynes which can efficiently produce conjugated diyne derivatives, while the use of a stoichiometric amount of copper salts, strong inorganic base, and excess oxidants is generally needed. Developing an environmentally friendly and effective method for the construction of symmetrical 1,3-diynes compounds by Glaser coupling is still highly desirable. In this study, we present an economical method for the production of symmetric diynes starting from various terminal acetylenes in a Glaser reaction. A simple and practical bis-N-heterocyclic carbene ligand has been introduced as efficient ligands for the Cu-catalyzed Glaser reaction. High product yields were obtained at 100 °C for a variety of substrates including aliphatic and aromatic terminal alkynes and differently substituted terminal alkynes including the highly sterically hindered substrate 2-methoxy ethynylbenzene or 2-trifluoromethyl ethynylbenzene and a series of functional groups, such as trifluoromethyl group, ester group, carboxyl group, and nitrile group. The established protocol is carried out in air under base-free condition and is operationally simple. These research work suggest that bis-N-heterocyclic carbene could also an appealing ligand for Glaser reaction and provide a reference for the preparation of symmetric 1,3-diynes in industrial filed. Full article

(This article belongs to the Special Issue π-Conjugated Functional Molecules & Polymers)

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11 pages, 2487 KiB

Open AccessArticle

Effect of Controlling Thiophene Rings on D-A Polymer Photocatalysts Accessed via Direct Arylation for Hydrogen Production

by Dongnai Ye, Lei Liu, Qimin Peng, Jiabin Qiu, Hao Gong, Aiguo Zhong and Shiyong Liu

Molecules 2023, 28(11), 4507; https://doi.org/10.3390/molecules28114507 - 1 Jun 2023

Cited by 74 | Viewed by 2444

Abstract

Conjugated polymer photocatalysts for hydrogen production have the advantages of an adjustable structure, strong response in the visible light region, adjustable energy levels, and easy functionalization. Using an atom- and step-economic direct C–H arylation method, dibromocyanostilbene was polymerized with thiophene, dithiophene, terthiophene, and fused thienothiophene and dithienothiophene, respectively, to produce donor–acceptor (D-A)-type linear conjugated polymers containing different thiophene derivatives with different conjugation lengths. Among them, the D-A polymer photocatalyst constructed from dithienothiophene could significantly broaden the spectral response, with a hydrogen evolution rate up to 12.15 mmol h⁻¹ g⁻¹. The results showed that the increase in the number of fused rings on thiophene building blocks was beneficial to the photocatalytic hydrogen production of cyanostyrylphene-based linear polymers. For the unfused dithiophene and terthiophene, the increase in the number of thiophene rings enabled more rotation freedom between the thiophene rings and reduced the intrinsic charge mobility, resulting in lower hydrogen production performance accordingly. This study provides a suitable process for the design of electron donors for D-A polymer photocatalysts. Full article

(This article belongs to the Special Issue π-Conjugated Functional Molecules & Polymers)

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Planned Papers

The below list represents only planned manuscripts. Some of these manuscripts have not been received by the Editorial Office yet. Papers submitted to MDPI journals are subject to peer-review.

Title: Dithienopyrrolobenzothiadiazole (DTPBT)-based Conjugated Molecules and Polymers
Author: Patel
Highlights: π-Conjugated organic molecules Ladder-type conjugated polymers Dithienopyrrolobenzothiadiazole

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