Polycyclic Aromatic Hydrocarbons as Potential Building Blocks for Organic Solar Cells

2019 ◽  
Vol 19 (6) ◽  
pp. 1142-1154 ◽  
Author(s):  
Cyril Aumaitre ◽  
Jean‐François Morin
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Solar Cells ◽  
Aromatic Hydrocarbons ◽  
Organic Solar Cells ◽  
Building Blocks ◽  
Polycyclic Aromatic

scholarly journals Site-Selective [2+2+n] Cycloadditions for Rapid, Scalable Access to Alkynylated Polycyclic Aromatic Hydrocarbons

2019 ◽  
Author(s):  
Gavin R. Kiel ◽  
Harrison Bergman ◽  
T. Don Tilley
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Aromatic Hydrocarbons ◽  
Structural Complexity ◽  
Building Blocks ◽  
Synthetic Methods ◽  
Proof Of Concept ◽  
Site Selectivity ◽  
Polycyclic Aromatic ◽  
Site Selective ◽  
Nanometer Regime

Polycyclic aromatic hydrocarbons (PAHs) are attractive synthetic building blocks for more complex conjugated nanocarbons, but their use for this purpose requires appreciable quantities of a PAH with reactive functional groups. Despite tremendous recent advances, most synthetic methods cannot satisfy these demands. Here we present a general and scalable [2+2+n] (n = 1 or 2) cycloaddition strategy to access PAHs that are decorated with synthetically versatile alkynyl groups and its application to seven structurally diverse PAH ring systems (thirteen new alkynylated PAHs in total). The critical discovery is the site-selectivity of an Ir-catalyzed [2+2+2] cycloaddition, which preferentially cyclizes tethered diyne units with preservation of other (peripheral) alkynyl groups. The potential for generalization of the site-selectivity to other [2+2+n] reactions is demonstrated by identification of a Cp<sub>2</sub>Zr-mediated [2+2+1] / metallacycle transfer sequence for synthesis of an alkynylated, selenophene-annulated PAH. The new PAHs are excellent synthons for macrocyclic conjugated nanocarbons. As a proof of concept, four were subjected to Mo catalysis to afford large, PAH-containing arylene ethylene macrocycles, which possess a range of cavity sizes reaching well into the nanometer regime. More generally, this work is a demonstration of how site-selective reactions can be harnessed to rapidly build up structural complexity in a practical, scalable fashion.

8,9-Didehydrofluoranthenes as Building Blocks for the Synthesis of Extended Polycyclic Aromatic Hydrocarbons (PAHs)

2001 ◽  
Vol 3 (20) ◽  
pp. 3115-3118 ◽  
Author(s):  
Wolf Dietrich Neudorff ◽  
Niels Schulte ◽  
Dieter Lentz ◽  
A. Dieter Schlüter
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Aromatic Hydrocarbons ◽  
Building Blocks ◽  
Polycyclic Aromatic

scholarly journals Boronic esters of corannulene: potential building blocks toward icosahedral supramolecules

2015 ◽  
Vol 2 (6) ◽  
pp. 626-633 ◽  
Author(s):  
Sara Da Ros ◽  
Anthony Linden ◽  
Kim K. Baldridge ◽  
Jay S. Siegel
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Aromatic Hydrocarbons ◽  
Building Blocks ◽  
Boronic Esters ◽  
Polycyclic Aromatic

Direct iridium-catalyzed multi-borylation provides a valuable tool for the symmetric functionalization of various polycyclic aromatic hydrocarbons, inter alia, regular fivefold derivatization of corannulene.

scholarly journals Dibenzoanthradiquinone Building Blocks for the Synthesis of Nitrogenated Polycyclic Aromatic Hydrocarbons

2020 ◽  
Vol 22 (12) ◽  
pp. 4737-4741
Author(s):  
Jose I. Martínez ◽  
Juan P. Mora-Fuentes ◽  
Marco Carini ◽  
Akinori Saeki ◽  
Manuel Melle-Franco ◽  
...  
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Aromatic Hydrocarbons ◽  
Building Blocks ◽  
Polycyclic Aromatic

scholarly journals Site-Selective [2+2+n] Cycloadditions for Rapid, Scalable Access to Alkynylated Polycyclic Aromatic Hydrocarbons

2019 ◽  
Author(s):  
Gavin R. Kiel ◽  
Harrison Bergman ◽  
T. Don Tilley
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Aromatic Hydrocarbons ◽  
Structural Complexity ◽  
Building Blocks ◽  
Synthetic Methods ◽  
Proof Of Concept ◽  
Site Selectivity ◽  
Polycyclic Aromatic ◽  
Site Selective ◽  
Nanometer Regime

Polycyclic aromatic hydrocarbons (PAHs) are attractive synthetic building blocks for more complex conjugated nanocarbons, but their use for this purpose requires appreciable quantities of a PAH with reactive functional groups. Despite tremendous recent advances, most synthetic methods cannot satisfy these demands. Here we present a general and scalable [2+2+n] (n = 1 or 2) cycloaddition strategy to access PAHs that are decorated with synthetically versatile alkynyl groups and its application to seven structurally diverse PAH ring systems (thirteen new alkynylated PAHs in total). The critical discovery is the site-selectivity of an Ir-catalyzed [2+2+2] cycloaddition, which preferentially cyclizes tethered diyne units with preservation of other (peripheral) alkynyl groups. The potential for generalization of the site-selectivity to other [2+2+n] reactions is demonstrated by identification of a Cp<sub>2</sub>Zr-mediated [2+2+1] / metallacycle transfer sequence for synthesis of an alkynylated, selenophene-annulated PAH. The new PAHs are excellent synthons for macrocyclic conjugated nanocarbons. As a proof of concept, four were subjected to Mo catalysis to afford large, PAH-containing arylene ethylene macrocycles, which possess a range of cavity sizes reaching well into the nanometer regime. More generally, this work is a demonstration of how site-selective reactions can be harnessed to rapidly build up structural complexity in a practical, scalable fashion.

scholarly journals Si-doped Polycyclic Aromatic Hydrocarbons: Synthesis and Opto-electronic Properties

2021 ◽  
Author(s):  
Thomas Delouche ◽  
Ghizlene Taifour ◽  
Marie cordier ◽  
Thierry Roisnel ◽  
Denis Tondelier ◽  
...  
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Aromatic Hydrocarbons ◽  
Building Blocks ◽  
Redox Properties ◽  
Electroluminescent Devices ◽  
Polycyclic Aromatic ◽  
Si Doped ◽  
Hydrocarbons Synthesis ◽  
The Impact ◽  
State Luminescence

We report the straightforward synthesis of Si-containing PAHs. The impact of pi-extension and exocyclic modifications on both the optical and redox properties is investigated using a joint experimental/theoretical approach. By taking advantage of the solid-state luminescence of these derivatives, electroluminescent devices are prepared. Such preliminary optoelectronic results highlight that these heteroatom-containing PAHs are promising building blocks for organic electronics.

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