A5030789900- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Synthesis and Properties of Aromatic Compounds
- Fullerene Chemistry and Applications
- Organic Electronics and Photovoltaics
- Graphene research and applications
- Perovskite Materials and Applications
- Conducting polymers and applications
- Molecular spectroscopy and chirality
- Axial and Atropisomeric Chirality Synthesis
- Photochromic and Fluorescence Chemistry
- Supramolecular Self-Assembly in Materials
- Asymmetric Synthesis and Catalysis
- Carbon Nanotubes in Composites
- Luminescence and Fluorescent Materials
- Molecular Junctions and Nanostructures
- Organic Chemistry Cycloaddition Reactions
- Advancements in Battery Materials
- Porphyrin and Phthalocyanine Chemistry
- DNA and Nucleic Acid Chemistry
- Cyclization and Aryne Chemistry
- Silicon and Solar Cell Technologies
- Chemical Synthesis and Analysis
- Quantum and electron transport phenomena
- Crystallography and molecular interactions
Hong Kong University of Science and Technology
2024-2025
University of Hong Kong
2024-2025
Chinese University of Hong Kong
2017-2024
University of Cologne
2023-2024
State Key Laboratory of Synthetic Chemistry
2024
University of California, Berkeley
2023
ConspectusNegatively curved carbons are theoretical carbon allotropes as proposed by embedding heptagons or octagons in a graphitic lattice. Unlike five-membered rings fullerenes, which induce positive curvature, the seven- eight-membered negative giving rise to variety of esthetic nanostructures known Mackay crystals schwarzites. In addition, hypothetical toroidal nanotubes consisting five-, six-, and seven-membered present curvature on outside inside torus. These with predicted have...
Abstract Indoor photovoltaics (IPVs) are garnering increasing attention from both the academic and industrial communities due to pressing demand of ecosystem Internet‐of‐Things. All‐polymer solar cells (all‐PSCs), emerging as a sub‐type organic photovoltaics, with merits great film‐forming properties, remarkable morphological light stability, hold promise simultaneously achieve high efficiency long‐term operation in IPV's application. However, dearth polymer acceptors medium‐bandgap has...
Abstract Giant dimeric acceptors (GDAs), a sub‐type of acceptor materials for organic solar cells (OSCs), have garnered much attention due to the synergistic advantages their monomeric and polymeric acceptors, forming well‐defined molecular structure with giant weight high efficiency stability. In this study, first time, two new GDAs, DYF‐V DY2F‐V are designed synthesized OSC operation, by connecting one vinylene linker mono‐/di‐fluorinated end group on Y‐series monomers, respectively. After...
This study puts forth two new members of fully ortho-benzannulated [ n]circulenes, heptabenzo[7]circulene and octabenzo[8]circulene, which are negatively curved nanographenes also represent unprecedented structures septuple [4]helicene octuple [4]helicene, respectively. The successful synthesis them through Scholl reaction in good to excellent yields takes advantage the reactivity naphthalene. Quantum chemistry calculations reveal that octabenzo[8]circulene both flexible π-molecules adopt...
This study presents a new type of negatively curved nanographene (C86 H32 ) that contains an unprecedented pattern heptagons. A tert-butylated derivative C86 was successfully synthesized using tetrabenzodipleiadiene as key building block. synthesis involved ring expansion reaction step to form the seven-membered rings in framework tetrabenzodipleiadiene. The single-crystal structure reveals saddle-shaped molecule with highly bent naphthalene moiety at center polycyclic backbone. As found...
Abstract Zigzag carbon nanobelts are a long‐sought‐after target for organic synthesis. Herein we report new strategies designing and synthesizing unprecedented zigzag nanobelts, which present wave‐like arrangement of hexagons in the unrolled lattice ( n ,0) single wall nanotubes =16 or 24). The precursors these hybrid cyclic arylene oligomers consisting meta ‐phenylene 2,6‐naphthalenylene as well para units. Scholl reactions form multiple carbon‐carbon bonds selectively at α‐positions...
Herein, we report the synthesis, structural analysis, optical and chiroptical properties of a novel quadruple helicene, which has two [6] [7]helicene moieties fused in contorted framework 92 sp2 carbon atoms. It was synthesized by Scholl reaction perylene-containing substrate with formation eight carbon-carbon bonds on perylene unit single synthetic operation. Chemical oxidation helicene tris(4-bromophenyl)ammoniumyl hexachloroantimonate resulted an air-stable dication, exhibits same...
This study explores a bottom-up approach toward negatively curved carbon allotropes from octabenzo[8]circulene, nanographene. Stepwise chemical reduction reactions of octabenzo[8]circulene with alkali metals lead to unique highly reduced hydrocarbon pentaanion, which is revealed by X-ray crystallography suggesting local view for the and metal intercalation processes allotropes. Polymerization tetrabromo derivative nickel-mediated Yamamoto coupling reaction results in new type porous...
Abstract Zigzag carbon nanobelts are a long‐sought‐after target for organic synthesis. Herein we report new strategies designing and synthesizing unprecedented zigzag nanobelts, which present wave‐like arrangement of hexagons in the unrolled lattice ( n ,0) single wall nanotubes =16 or 24). The precursors these hybrid cyclic arylene oligomers consisting meta ‐phenylene 2,6‐naphthalenylene as well para units. Scholl reactions form multiple carbon‐carbon bonds selectively at α‐positions...
The synthesis of new carbazole-fused polycyclic aromatics with interesting geometry and useful properties was explored using Scholl reactions. As found from the reactions substrates having two carbazole units linked at different positions through o-phenylene, oxidative coupling occurred in a regioselective manner carbon-carbon bonds preferably formed C3 C4 N-alkyl carbazoles. A N-containing aromatic bowl characterized by single-crystal X-ray crystallography, p-type organic semiconductors...
Two molecular nanocarbons result from merging a negatively curved nanographene and carbon nanoring in two constitutional isomers of D2 C2v symmetry, respectively. They were synthesized by attachment C-shaped paraphenylene precursors to 2,11,18,27-tetrabromooctabenzo[8]circulene the subsequent intramolecular Yamamoto coupling reductive aromatization reactions. The flexible nature octabenzo[8]circulene enabled different ways connection reactions, leading isomers. isomer is shaped like figure...
A new armchair carbon nanobelt is successfully synthesized by tuning the regioselectivity of Scholl reaction 1,1':2',1'':4'',1''':2''',1''''-quinquephenyl. This exhibits a preferential binding affinity towards C
Abstract This study presents a new type of negatively curved nanographene (C 86 H 32 ) that contains an unprecedented pattern heptagons. A tert ‐butylated derivative C was successfully synthesized using tetrabenzodipleiadiene as key building block. synthesis involved ring expansion reaction step to form the seven‐membered rings in framework tetrabenzodipleiadiene. The single‐crystal structure reveals saddle‐shaped molecule with highly bent naphthalene moiety at center polycyclic backbone. As...
Abstract Herein, we report the synthesis, structural analysis, optical and chiroptical properties of a novel quadruple helicene, which has two [6] [7]helicene moieties fused in contorted framework 92 sp 2 carbon atoms. It was synthesized by Scholl reaction perylene‐containing substrate with formation eight carbon‐carbon bonds on perylene unit single synthetic operation. Chemical oxidation helicene tris(4‐bromophenyl)ammoniumyl hexachloroantimonate resulted an air‐stable dication, exhibits...
Abstract This study puts forth a novel terminal group design to develop medium‐band gap Y‐series acceptors beyond conventional side‐chain engineering. We focused on the strategical integration of an electron‐donating methoxy and electron‐withdrawing halogen atom at benzene‐fused groups. combination precisely modulated dipole moment electron density groups, effectively attenuating intramolecular charge transfer effect, widening band acceptors. The incorporation these groups yielded two...
Multiple helicenes display distinct aromatic cores characterized by highly twisted rings that are shared or fused with constituent helicene moieties. Diversifying these unlocks avenues for creating multiple properties and topologies. Herein we report the synthesis of a quadruple[6]helicene featuring pyrene as core. The involved key steps annulative π-extension reaction Scholl reaction. By extending along axial direction, degree contortion core can be controlled from nearly flat to twisted....
Herein, we report robust π-conjugated radical cations resulting from the oxidation of hexabenzoperylene (HBP) derivatives, HBP-B and HBP-H, which have butyl hexyl groups, respectively, attached to same twisted double helicene π-backbone. The cation was successfully crystallized in form hexafluorophosphate, exhibited conductivity as high 1.32 ± 0.04 S cm-1. Photochemical HBP-H by molecular oxygen led formation its solid state, found with different techniques. This allowed organic field effect...
Synthesis of an unprecedented aromatic saddle consisting 80 sp2 carbons is enabled by including naphthylene groups in the substrate Scholl reaction. The negatively curved polycyclic framework this revealed single crystal X-ray crystallography, and its stereodynamics are studied with density functional theory calculations.
Abstract This study puts forth a novel terminal group design to develop medium‐band gap Y‐series acceptors beyond conventional side‐chain engineering. We focused on the strategical integration of an electron‐donating methoxy and electron‐withdrawing halogen atom at benzene‐fused groups. combination precisely modulated dipole moment electron density groups, effectively attenuating intramolecular charge transfer effect, widening band acceptors. The incorporation these groups yielded two...
Exercising direct control over the unusual electronic structures arising from quantum confinement effects in graphene nanoribbons (GNRs) is intimately linked to geometric boundary conditions imposed by structure of ribbon. Besides composition and position substitutional dopant atoms, symmetry unit cell, width, length, termination a GNR govern its structure. Here, we present rational design that integrates each these interdependent variables within modular bottom-up synthesis. Our hybrid...
Abstract The synthesis of new carbazole‐fused polycyclic aromatics with interesting geometry and useful properties was explored using Scholl reactions. As found from the reactions substrates having two carbazole units linked at different positions through o ‐phenylene, oxidative coupling occurred in a regioselective manner carbon–carbon bonds preferably formed C3 C4 N‐alkyl carbazoles. A N‐containing aromatic bowl characterized by single‐crystal X‐ray crystallography, p‐type organic...
We herein report the reactivity and regioselectivity of 2-pyrenyl as a coupling unit in Scholl reactions. On basis reactions hexaarylbenzene substrates, we have found that pyrenyl units are preferably oxidized over naphthyl phenyl under appropriate reaction conditions, allowing divergent synthesis through highly controllable intramolecular sequence. The C1 C3 positions favorable sites for while C4 is not reactive to allow further coupling. pattern can be explained by spin density...