Bent Naphthodithiophenes: Synthesis and Characterisation of Isomeric Fluorophores DOI Creative Commons
Emmanuel Bentil Asare Adusei,

Vincent Casetti,

Calvin D. Goldsmith

et al.

Published: June 26, 2024

Thiophene-containing heteroarenes are one of the most well-known classes π-conjugated building blocks for photoactive molecules. Isomeric naphthodithiophenes (NDTs) at forefront this research area due to their straightforward synthesis and derivatization. Notably, NDT geometries that bent – such as naphtho[2,1-b:3,4-b’]dithiophene (α-NDT) naphtho[1,2-b:4,3-b’]dithiophene (β -NDT) seldom employed small This report investigates how remote substituents impact photophysical properties isomeric α- β-NDTs. The orientation thiophene units plays a critical role in emission: α(OHex)R2 series conjugation from end-caps core is apparent, while β(Oi-Pent)R2 minimal change observed unless strong electron acceptors, β(Oi-Pent)(PhCF3)2, employed. push-pull Acceptor–Donor–Acceptor (A–D–A) fluorophore exhibits positive fluorosolvatochromism correlates with increasing solvent polarity parameter, ET(30). In total, these results highlight able modulate emission NDTs.

Language: Английский

Self-Assembly of Functionalized Twistarenes into Supramolecular Assemblies with Chiroptical Property and Photoconductive Behavior DOI

Zewei Qi,

Sujuan Wang,

Bingliang Ji

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(4), P. 781 - 785

Published: Jan. 19, 2024

A pair of novel chiral 1-phenylethylamine-modified twistarenes (4 and 11; compound 4 = 9,14-di-tert-butyl-7,16-diphenyl-2-(1-phenylethyl)-1H-benzo[8',9']triphenyleno[2',3':6,7]fluoreno[2,1,9-def]isoquinoline-1,3(2H)-dione) have been synthesized characterized, how the solvent component affects chirality transfer their self-assembled processes is investigated in mixtures with THF H2O. The ordered assembly 11 exhibits circular dichroism response. In addition, both 11a 11b display positive photoconducting behavior.

Language: Английский

Citations

4

Post-functionalization of end-capped twistacenes with pyrene units DOI
Sujuan Wang,

Tongtong Ye,

Jinchong Xiao

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5638 - 5669

Published: Jan. 1, 2024

This review covers recent advances in post-functionalization of twistacenes to realize polyacenes, chiral nanographenes and their semiconductor properties, emphasizing a promising future for constructing nanotubes.

Language: Английский

Citations

3

Chiral nanographenes exhibiting circularly polarized luminescence DOI Creative Commons
V. Ravi Kumar,

J. Páez,

Sandra Míguez‐Lago

et al.

Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Chiral nanographenes: molecular architecture, key constituents, and their circularly polarized luminescence.

Language: Английский

Citations

0

Synthesis of Thiophene‐fused Helicenes DOI Creative Commons
Victorino Vallejos González, Justin Kahle, Christopher Hüßler

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(33)

Published: July 5, 2023

Abstract The synthesis of three penta‐ and hexahelicenes containing two terminal thiophene units is described. syntheses pentahelicenes consist 1,4‐bisalkynylation a benzene precursor double Suzuki coupling in 2,3‐position to introduce units. ortho , ’ fusion yielding the final products was achieved with Fürstner's protocol using platinum(II) chloride or JohnPhos‐complexed gold(I) as catalysts. A similar approach started naphthalene derivative, where 2,7‐bisalkynylation subsequent thiophene‐2‐boronic acid at 1,8‐position furnished precursors, which respective or, favourably, indium(III) chloride. UV/Vis spectra cyclic voltammograms were recorded for all helicenes HOMO/LUMO gaps calculated DFT methods.

Language: Английский

Citations

6

Heptagon-Embedded Helicene Derivatives: Synthesis, Crystal Structural Analyses, and Circularly Polarized Luminescence DOI

Zewei Qi,

Honglin Shang,

Bingliang Ji

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(20), P. 14550 - 14558

Published: Oct. 9, 2023

Two pairs of isomers heptagon-embedded helical arenes (3/6 and 10/13) have been strategically prepared, where the molecular structures 3 13 identified through single crystal X-ray diffraction analysis. The effect heptagon unit on physical properties 3, 6, 10, is investigated in a comparative manner, results indicate that optical enantiomers obtained from HPLC exhibit promising chiroptical properties.

Language: Английский

Citations

6

Straightforward Synthesis of Pentagon‐Embedded Expanded [11]Helicenes for Radiative Cooling Property DOI

Bingliang Ji,

Zewei Qi,

Tongtong Ye

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 30(3)

Published: Oct. 23, 2023

Two new pentagon-embedded carbo[11]helicenes have been designed and synthesized in a three-step process, which are the first example of through post-functionalization twistacene. TD-DFT analyses indicate that both them possess high enantiomerization barriers 42.29 kcal/mol 40.76 kcal/mol, respectively. They emit strong red fluorescence can be chemically oxidized into stable cationic radicals upon addition AgSbF

Language: Английский

Citations

5

Coumarin-embedded [5]helicene derivatives: synthesis, X-ray analysis and photoconducting properties DOI
Hui Yang, Guofeng Chen, Ran Zhang

et al.

Nanoscale, Journal Year: 2024, Volume and Issue: 16(10), P. 5395 - 5400

Published: Jan. 1, 2024

Two novel coumarin-embedded π-extended [5]helicene derivatives (3a and 6a) have been strategically synthesized characterized, the structure of 3a was determined via single crystal X-ray analysis.

Language: Английский

Citations

1

Bent naphthodithiophenes: synthesis and characterization of isomeric fluorophores DOI Creative Commons
Emmanuel Bentil Asare Adusei,

Vincent Casetti,

Calvin D. Goldsmith

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(35), P. 25120 - 25129

Published: Jan. 1, 2024

Thiophene-containing heteroarenes are one of the most well-known classes π-conjugated building blocks for photoactive molecules. Isomeric naphthodithiophenes (NDTs) at forefront this research area due to their straightforward synthesis and derivatization. Notably, NDT geometries that bent - such as naphtho[2,1-

Language: Английский

Citations

1

π-Expanded [6]Helicene-Containing Nanographenes: Synthesis, Structures, and Chiroptical Properties DOI

Tongtong Ye,

Yiming Li,

Yanwei Shi

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(34), P. 7088 - 7093

Published: Aug. 15, 2024

A family of chiral nanographenes bearing [6]helicene units has been synthesized via the classical Scholl reaction. Inserting unit into parent nanographene skeleton can result in different structural topologies and optoelectric properties. Moreover, isolated enantiomers exhibit attractive chiroptical

Language: Английский

Citations

1

Expanded furan-containing helicene π-systems: Synthesis, crystal analyses, physical and photoswitching properties DOI
Ran Zhang, Guofeng Chen, Hui Yang

et al.

Dyes and Pigments, Journal Year: 2023, Volume and Issue: 212, P. 111127 - 111127

Published: Jan. 25, 2023

Language: Английский

Citations

2