Spiro‐Fused vs 575‐Ringed Boron‐Doped Polycyclic π‐Systems: Selective Synthesis, Reactivity and Properties DOI Open Access
Yujia Liu, Xinyu Tian, Zeyi Li

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 12, 2024

Abstract Incorporation of heteroatoms and/or non‐hexagonal rings into polycyclic aromatic hydrocarbons (PAHs) can alter their intrinsic structures and physical properties. However, it is challenging to construct PAHs featuring boron/carbon composition combination. Herein, we disclose the selective synthesis spiro‐type pentagon/heptagon‐containing boron‐doped π‐systems by Scholl reaction. Two spiro‐fused organoboranes 1 2 one 575‐ringed nanographene 3 were synthesized. The key point that boron‐edged π‐system enabled unexpected spiro‐formation via dearomatization, whereas boron‐centered desired π‐extension cyclodehydrogenation. thus‐obtained molecules exhibit intriguing but fully distinct reactivity, electronic properties, for instance, while may react with Brønsted acid display reversible chemochromism further convert , possesses very broad absorption, short excited‐state lifetime no fluorescence nature. As disclosed, boron atom together spirocycle region or structural motif significantly contribute characteristic Thus, this study sheds light on control over reaction using organoborane will promote exploration more sophisticated as organic reactive optical scaffolds.

Language: Английский

Single-Crystal-to-Single-Crystal Photosynthesis of Supramolecular Organoboron Polymers with Dynamic Effects DOI
Subhrajyoti Bhandary, Marek Beliš, Rahul Shukla

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(12), P. 8659 - 8667

Published: Feb. 26, 2024

The solid-state synthesis of single-crystalline organic polymers, having functional properties, remains an attractive and developing research area in polymer chemistry materials science. However, light-triggered topochemical crystalline polymers comprising organoboron backbone has not yet been reported. Here, we describe intriguing example single-crystal-to-single-crystal (SCSC) rapid photosynthesis (occurs on a seconds-scale) two structurally different linear driven by environmentally sustainable visible/sun light, obtained from the same monomer molecule. A newly designed Lewis acid-base type molecular B ← N adduct (consisting core naphthylvinylpyridine ligands) crystallizes forms featuring chemical structure but 3D structural topologies, namely, monomers

Language: Английский

Citations

20
Constructing Covalent Organic Polymers through Dative B─N Bonds: Synthesis, Single Crystal Structures, and Physical Properties DOI Creative Commons
Xin Wang, Lei Zhang, Xiang Wang

et al.

Advanced Functional Materials, Journal Year: 2024, Volume and Issue: unknown

Published: March 10, 2024

Abstract Growing single crystals of covalent organic polymers (COPs) for single‐crystal X‐ray diffraction analysis is very important and highly desirable because such strategy provides a deep understanding crystallization kinetics the structure‐property relationship COPs. Based on that dynamic bonds can allow self‐correction structures during crystal growth, two COPs ( CityU‐15 CityU‐16 ) based dative boron‐nitrogen (B─N) have been successfully obtained. Detailly, tetra(4‐pyridyl)tetrathiafulvalene (TTF(py) 4 tetra(4‐pyridyl)porphine (TPYP) are employed as N‐donor ligands to react with 1,4‐bis(benzodioxaborole) benzene prepare COPs, named , respectively. exhibits enhanced stability compared size reach up 0.7 cm. shows good recyclability reveals noticeable photosensitivity upon iodine doping. After treatment iodine, both display obvious color changes. Specially, device I 2 ‐treated excellent low‐voltage operation low energy consumption 3.3 fJ, facilitating development artificial vision. This work highlights successful introduction functional groups into B‐N‐containing opening new avenues expanding their applications.

Language: Английский

Citations

15
Adaptive and Robust Vitrimers Fabricated by Synergy of Traditional and Supramolecular Polymers DOI
Jiao Wang, Wei You, Liya Chen

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(23)

Published: April 8, 2024

Abstract Vitrimers offer a unique combination of mechanical performance, reprocessability, and recyclability that makes them highly promising for wide range applications. However, achieving dynamic behavior in vitrimeric materials at their intended usage temperatures, thus combining reprocessability with adaptivity through associative covalent bonds, represents an attractive but formidable objective. Herein, we couple boron‐nitrogen (B−N) dative bonds B−O to generate new class vitrimers, vitrimers (BNVs), endow features temperatures. Compared boron‐ester (BEVs) without B−N the BNVs showcase enhanced performance. The excellent properties come from synergistic effect supramolecular polymer networks. Moreover, benefiting exchange above topological freezing temperature ( T v ), resultant also possess processability. This study leveraged structural characteristics boron‐based vitrimer achieve material reinforcement toughness enhancement, simultaneously providing novel design concepts construction materials.

Language: Английский

Citations

12
Adaptive and Robust Vitrimers Fabricated by Synergy of Traditional and Supramolecular Polymers DOI
Jiao Wang, Wei You, Liya Chen

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(23)

Published: April 8, 2024

Abstract Vitrimers offer a unique combination of mechanical performance, reprocessability, and recyclability that makes them highly promising for wide range applications. However, achieving dynamic behavior in vitrimeric materials at their intended usage temperatures, thus combining reprocessability with adaptivity through associative covalent bonds, represents an attractive but formidable objective. Herein, we couple boron‐nitrogen (B−N) dative bonds B−O to generate new class vitrimers, vitrimers (BNVs), endow features temperatures. Compared boron‐ester (BEVs) without B−N the BNVs showcase enhanced performance. The excellent properties come from synergistic effect supramolecular polymer networks. Moreover, benefiting exchange above topological freezing temperature ( T v ), resultant also possess processability. This study leveraged structural characteristics boron‐based vitrimer achieve material reinforcement toughness enhancement, simultaneously providing novel design concepts construction materials.

Language: Английский

Citations

5
Poly(iminoborane)s with Aromatic Side Groups: Insights into the Microstructure from Monodisperse Model Oligomers DOI Creative Commons
Matthias Maier, Alexandra Friedrich,

Johannes S. Schneider

et al.

ChemistryEurope, Journal Year: 2024, Volume and Issue: 2(2)

Published: Feb. 6, 2024

Abstract While certain inorganic main‐group polymers such as silicones (polysiloxanes) are ubiquitous in our everyday life, poly(iminoborane)s have been elusive for a long time. Incorporation of heterocyclic building blocks into their backbone has recently enabled access to the first derivatives this inorganic‐polymer class, approach effectively prevents undesired side‐reactions borazines. Information about microstructure these cyclolinear macromolecules, however, scarce. Herein, we present synthesis series monodisperse oligomers with up 7 boron and 8 nitrogen atoms, representing longest well‐defined molecular [>B=N<] x chain date. We accomplished characterize six them structurally solid state by single‐crystal X‐ray diffraction, thus providing valuable insight poly(iminoborane)s. In addition, report on new poly(iminoborane) featuring aryl side groups, an increased content unsubstituted phenyl groups. The p ‐( n ‐butyl)phenyl‐substituted species 13 represents highest‐molecular‐weight sample class

Language: Английский

Citations

4
Polymeric bis(triphenylphosphine)iminium chloride as a recyclable catalyst DOI Creative Commons
Ziwei Xu, Meng Wang, Michael P. Shaver

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(38), P. 15745 - 15750

Published: Jan. 1, 2024

The powerful PPNCl catalyst can be converted into a recyclable and more soluble polymeric version through post-polymerisation modification of triphenylphosphine-decorated copolymer.

Language: Английский

Citations

3
Recent Advances of Boron‐Containing Chiral Luminescent Materials† DOI Open Access

Jiaqi Di,

Shuran Han,

Pangkuan Chen

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 25, 2024

Comprehensive Summary As a class of organic dyes, boron‐containing compounds play an important role in luminescent materials. They have attracted considerable attention due to their unique photophysical properties. Chiral systems wide range practical applications biological imaging, optoelectronic devices, information storage and 3D display. Boron‐containing chiral materials can not only effectively improve the properties CPL materials, but also bring system, which enables them be used as favorable emitting for expanded applications. Here, we review research progress by detailed discuss according different skeletons, such point chirality, 1,1’‐binaphthyl, [ n ]helicenes, [2,2]paracyclophane pillar[5]arenes. We believe that this is significance development Key Scientists The studies circularly polarized luminescence (CPL) based on small molecules advanced significantly. However, gained recent years. In 2019, Zhao's group prepared binaphthalene derivative modified with triarylborane, representing molecule material exhibit characteristics responsive both solvent fluoride ions. 2020, Chen's steric effects triarylborane triphenylamine prepare planar 2021, Wang's developed new B,N‐embedded double hetero[7]helicenes strong chiroptical responses UV‐visible region. same year, He's asymmetric reactions synthesize boron‐based point‐chirality high efficiency enantioselectivity. 2023, Ravat synthesized 1,4‐B,N‐embedded helicenes exhibiting narrow‐band fluorescence CPL. During period, Matthias Wagner et al obtained (BO) 2 ‐doped tetrathia[7]helicene via efficient four‐step synthesis, Zheng reported nearly pure green electroluminescent device (CP‐OLED). 2024, hetero‐[9]helicenes offering pathway towards significantly enhanced helicene‐based CPEL.

Language: Английский

Citations

3
Intrinsic stimuli-responsive main-chain supramolecular polymers driven by dative B←N bonds DOI
X. L. Ji, Zi-Hao Wang, Wei Yuan

et al.

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A novel main-chain supramolecular polymer (MCSP) with intrinsic stimuli-responsiveness based on dative B ← N bonds has been successfully developed.

Language: Английский

Citations

0
Creation of photofunctional materials through supramolecular complex formation and host–guest chemistry DOI
Toshikazu Ono

Journal of Inclusion Phenomena and Macrocyclic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: April 23, 2024

Language: Английский

Citations

2
Confinement and Separation of Benzene from an Azeotropic Mixture Using a Chlorinated B←N Adduct DOI Creative Commons
Isabella J. Jupiter, Jesus Daniel Loya, Nicholas Lutz

et al.

Crystal Growth & Design, Journal Year: 2024, Volume and Issue: 24(14), P. 5883 - 5888

Published: June 26, 2024

Separations of azeotropic mixtures are typically carried out using energy-demanding processes (e.g., distillation). Here, we report the capacity a self-assembled chlorinated boronic ester-based adduct to confine acetonitrile and benzene in channels upon crystallization. The solvent confinement occurs via combination hydrogen bonding [π···π] interactions. Quantitative separation from an 1:1 mixture benzene/acetonitrile (v/v), methanol is achieved through crystallization with by complementary [C–H···O] [C–H···π] Inclusion behavior rationalized molecular modeling crystallographic analysis. ester shows potential modularity isosteric substitution for challenging chemical azeotropes).

Language: Английский

Citations

2