Poly(arylene iminoborane)s, Analogues of Poly(arylene vinylene) with a BN‐Doped Backbone: A Comprehensive Study DOI Creative Commons
Matthias Maier,

Johannes Chorbacher,

Anna Hellinger

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(69)

Published: Sept. 19, 2023

Despite the great success of concept doping organic compounds with BN units to access new materials tailored properties, its use in polymer chemistry has only been realized quite recently. Herein, we present a comprehensive study oligo- and poly(arylene iminoborane)s comprising backbone phenylene or thiophene moieties, as well combinations thereof, linked via B=N units. The novel polymers can be regarded analogues poly(p-phenylene vinylene) (PPV) poly(thiophene (PTV) their copolymers. Our modular synthetic approach allowed us prepare four 12 monodisperse oligomers modulated electronic properties. Alternating electron-releasing diaminoarylene electron-accepting diborylarylene building blocks gave rise pronounced donor-acceptor character. Effective π-conjugation over arylene iminoborane is evidenced by systematic bathochromic shifts low-energy UV-vis absorption maximum increasing chain length, which furthermore supported crystallographic computational investigations. Furthermore, all investigated show emission visible light solid state aggregation-induced (AIE) behavior, due presence partially flexible linear linkages backbone.

Language: Английский

Organoboron-based multiple-resonance emitters: synthesis, structure–property correlations, and prospects DOI Creative Commons
Masashi Mamada, Masahiro Hayakawa, Junki Ochi

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(3), P. 1624 - 1692

Published: Jan. 1, 2024

This review highlights organoboron-based multiple-resonance compounds’ synthetic strategies classified as one-pot borylation, one-shot and late-stage functionalisation, explores material structure–photophysical property correlations.

Language: Английский

Citations

126
Recent synthetic strategies of small heterocyclic organic molecules with optoelectronic applications: a review DOI
Ramsha Iftikhar,

Faiza Zahid Khan,

Naila Naeem

et al.

Molecular Diversity, Journal Year: 2023, Volume and Issue: 28(1), P. 271 - 307

Published: Jan. 7, 2023

Language: Английский

Citations

37
Multiple Helicenes Defected by Heteroatoms and Heptagons with Narrow Emissions and Superior Photoluminescence Quantum Yields** DOI

Dehui Tan,

Jiaqi Dong,

Tinghao Ma

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(29)

Published: May 18, 2023

The incorporation of heteroatoms and/or heptagons as the defects into helicenes expands variety chiroptical materials with novel properties. However, it is still challenging to construct boron-doped heptagon-containing high photoluminescence quantum yields (PLQYs) and narrow full-width-at-half-maximum (FWHM) values. We report an efficient scalable synthesis a quadruple helicene 4Cz-NBN two nitrogen-boron-nitrogen (NBN) units double 4Cz-NBN-P1 bearing NBN-doped heptagons, latter could be formed via two-fold Scholl reaction former. exhibit excellent PLQYs up 99 % 65 FWHM 24 nm 22 nm, respectively. emission wavelengths are tunable stepwise titration experiments toward fluoride, enabling distinguished circularly polarized luminescence (CPL) from green, orange (4Cz-NBN-P1-F1) yellow (trans/cis-4Cz-NBN-P1-F2) near-unity broader circular dichroism (CD) ranges. five structures aforementioned four were confirmed by single crystal X-ray diffraction analysis. This work provides design strategy for construction non-benzenoid multiple exhibiting emissions superior PLQYs.

Language: Английский

Citations

36
Stereoselective formation of boron-stereogenic organoboron derivatives DOI Creative Commons

Amel Abdou-Mohamed,

Clara Aupic,

Corentin Fournet

et al.

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(13), P. 4381 - 4391

Published: Jan. 1, 2023

Four-coordinate organoboron derivatives present interesting chemical, physical, biological, electronical, and optical properties. Given the increasing demand for synthesis of smart functional materials based on chiral compounds, exploration stereoselective boron-stereogenic organo-derivatives is highly desirable. However, construction compounds stereogenic at boron has been far less studied than other elements main group due to configurational stability concerns. Nowadays, these species are no longer elusive configurationally stable have highlighted. The idea show potential building four-coordinate centre encourage future endeavors developments in field.

Language: Английский

Citations

26
Recent Advances in Boron‐Containing Acenes: Synthesis, Properties, and Optoelectronic Applications† DOI

Yongkang Guo,

Cheng Chen, Xiaoye Wang

et al.

Chinese Journal of Chemistry, Journal Year: 2022, Volume and Issue: 41(11), P. 1355 - 1373

Published: Dec. 31, 2022

Comprehensive Summary Acenes with linearly fused benzene rings have attracted much attention due to their intriguing optical and electronic properties. Nevertheless, the poor ambient stability of longer acenes has hampered investigation physicochemical properties potential applications. The incorporation main group elements into acene backbones provides a viable strategy enhance stability, meanwhile, generates new family heteroatom‐doped (namely heteroacenes) modified functions. In particular, boron‐containing represent an attractive class heteroacenes owing existence vacant p orbital boron, which endows π‐conjugated systems appealing features, such as Lewis acidity, electron‐accepting capability, stimuli‐responsivity, adjustable photophysical During past decade, significant progress been achieved in synthesis applications acenes, but focused review on this topic elusive. Here, we summarize recent advances studies covering synthesis, properties, various electroluminescence devices, well biosensors, etc . We hope that timely will stimulate research interest unique materials promote optoelectronic

Language: Английский

Citations

25
A Free Phosphaborene Stable at Room Temperature DOI
Jiancheng Li,

Zhihao Lu,

Liu Leo Liu

et al.

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(51), P. 23691 - 23697

Published: Dec. 15, 2022

Free phosphaborenes (R-P═B-R) are PB analogues of alkynes, and their isolation is a long-sought-after goal. Herein, we demonstrate that the combination π-donating π-accepting substituent with bulky flanking arene rings enables crystalline free phosphaborene 5 at room temperature. This electron push-pull cooperation, combined kinetic protection, hinders its inherent tendency to oligomerize. species features double bond consisting conventional σ delocalized π bond. The lone pair electrons P slightly contributes bonding. Preliminary reactivity studies show undergoes facile (cyclo)addition reactions p-methyl benzaldehyde, p-fluoroacetophenone, carbon disulfide, last which results in cleavage. Our strategy has significant impact on future synthesis ambiphilic heterodiatomic multiply bonded main group species.

Language: Английский

Citations

21
Precise synthesis of BN embedded perylene diimide oligomers for fast-charging and long-life potassium–organic batteries DOI Creative Commons
Guangwei Shao, Huan Liu,

Li Chen

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(9), P. 3323 - 3329

Published: Jan. 1, 2024

Three BN bridged PDI oligomers are synthesized and the orientations precisely regulated in two trimers. All new compounds show great improvement voltage potential, rate performance cyclic stability potassium–organic batteries.

Language: Английский

Citations

5
NBN‐ and BNB‐Phenalenyls: the Yin and Yang of Heteroatom‐doped π Systems DOI Creative Commons
Alexander Scholz,

Julian Gerhard Massoth,

Lennart Stoess

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(27)

Published: March 1, 2024

Abstract NBN‐ and BNB‐doped phenalenyls are isoelectronic to phenalenyl anions cations, respectively. They represent a pair of complementary molecules that have essentially identical structures but opposite properties as electron donors acceptors. The NBN‐phenalenyls 1 – 4 considered here were prepared from N , N’‐ dimethyl‐1,8‐diaminonaphthalene readily available boron‐containing building blocks (i. e., BH 3 ⋅SMe 2 ( ), p ‐CF ‐C 6 H B(OH) C 5 or MesBCl / i Pr NEt )). Treatment with 4‐Me N‐2,6‐Me Li gave the corresponding NBN derivative . BNB‐phenalenyl was synthesized 1,8‐naphthalenediyl‐bridged diborane(6), PhNH MesMgBr. A computational study reveals photoemission originates locally excited (LE) states at NBN‐phenalenyl fragments, while is dominated by charge transfer (CT) fragment. Depending on dihedral angle θ between its Ph planes, compound emits mainly less polar LE >55°) more CT state <55°). In turn, energetic preference for either governed polarity solvent used. An equimolar aggregate BNB‐phenalenyls (in THF/H O) shows distinct red‐shifted emission compared individual components, which an intermolecular state.

Language: Английский

Citations

4
NBN/BNB-doped phenalenyl homo- and heterodyads: structural uniformity but optoelectronic diversity DOI Creative Commons
Alexander Scholz, Thomas Froitzheim, Michael Bolte

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(11), P. 3109 - 3118

Published: Jan. 1, 2024

Phenylene-bridged homo- and heterodyads of NBN- BNB-phenalenyls were synthesized. The show ambipolar redox character aggregation-induced emission in the solid state.

Language: Английский

Citations

4
Tetramerization of BEB-Doped Phenalenyls to Obtain (BE)8-[16]Annulenes (E = N, O) DOI
Alexander Scholz, Michael Bolte, A.V. Virovets

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(17), P. 12100 - 12112

Published: April 18, 2024

Two (BE)8-[16]annulenes were prepared and fully characterized by experimental quantum-chemical means (1, E = N; 2, O). The 1,8-naphthalenediyl-bridged diborane(6) 3 served as their common starting material, which was treated with [Al(NH3)6]Cl3 to form 1 (91% yield) or 1,8-naphthalenediboronic acid anhydride 2 (93% yield). As a result, the heteroannulenes are supported four aromatic "clamps" may also be viewed NH- O-bridged cyclic tetramers of BNB- BOB-doped phenalenyls. X-ray crystallography on mono-, di-, tetraadducts 2·thf, 2·py2, 2·py4 showed that is an oligotopic Lewis (thf/py: tetrahydrofuran/pyridine donor). applicability basic ligand in coordination chemistry demonstrated synthesis mononuclear Ag+ complex [Ag(py)2(2·py4)]+ dinuclear Pb2+ 6. During assembly 6, rearrangement led formation two (BO)9-macrocycles linked BOB-phenalenyls nanometer-sized cage negatively charged, tetracoordinated B atoms. Both show several redox waves cathodic regions voltammograms. An in-depth assessment consequences electron injection aromaticity achieved electronic structure calculations. proposed exhibit switching capabilities [16]annulene motif.

Language: Английский

Citations

4