scholarly journals Efficient synthetic methods for the installation of boron–nitrogen bonds in conjugated organic molecules

2016 ◽  
Vol 45 (14) ◽  
pp. 5920-5924 ◽  
Author(s):  
Matthew M. Morgan ◽  
Warren E. Piers
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Aromatic Hydrocarbons ◽  
Organic Molecules ◽  
Synthetic Methods ◽  
Conjugated Organic Molecules ◽  
Polycyclic Aromatic ◽  
Device Applications ◽  
Nitrogen Bonds ◽  
Boron Nitrogen

New synthetic methods for preparing gram quantities BN analogs of polycyclic aromatic hydrocarbons are highlighted. Such methods are key to proper evaluation of these materials in device applications.

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.

Bottom-Up Synthesis of Nitrogen-Doped Polycyclic Aromatic Hydrocarbons

Synlett ◽  
2019 ◽  
Vol 31 (03) ◽  
pp. 211-222
Author(s):  
Junzhi Liu ◽  
Xinliang Feng
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Organic Synthesis ◽  
Aromatic Hydrocarbons ◽  
Efficient Method ◽  
Dipolar Cycloaddition ◽  
Bottom Up ◽  
Nitrogen Doped ◽  
Synthesis Strategy ◽  
Polycyclic Aromatic ◽  
Boron Nitrogen

Bottom-up organic synthesis serves as an efficient method to provide atomically precise heteroatom-doped polycyclic aromatic hydrocarbons (PAHs) with not only well-defined size and edge structures but also specific concentrations and positions of the heteroatoms. We provide a plenary account of the preparation of nitrogen-doped PAHs (N-PAHs) through 1,3-dipolar cycloaddition between different dipolarophiles, as well as pyrazine-type N-doped diaza-hexa-peri-hexabenzocoronene (diaza-HBC). Additionally, we present the synthesis of a class of helical N-charged PAHs, including one charged aza[5]helicene and two charged aza[4]helicenes. Moreover, the bottom-up organic synthesis strategy is further extended to the construction of novel nitrogen-boron-nitrogen (NBN)-containing PAHs. Finally, we discuss the synthesis of four-coordinate boron chromophores containing 6,12,18-tris(alkyl amine)-5,11,17-triazatrinaphthylene derivative ligands.1 Introduction2 Nitrogen-Doped PAHs Based on Dibenzo-9a-azaphenalene (DBAP)3 Cationic Nitrogen-Doped Helical PAHs4 Nitrogen–Boron–Nitrogen-Doped PAHs5 Conclusion and Outlook

En Route to Stimuli-Responsive Boron-, Nitrogen-, and Sulfur-Doped Polycyclic Aromatic Hydrocarbons

2016 ◽  
Vol 22 (37) ◽  
pp. 13181-13188 ◽  
Author(s):  
Valentin M. Hertz ◽  
Julian G. Massoth ◽  
Michael Bolte ◽  
Hans-Wolfram Lerner ◽  
Matthias Wagner
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Aromatic Hydrocarbons ◽  
Stimuli Responsive ◽  
Polycyclic Aromatic ◽  
Boron Nitrogen

Aggregation Effects on Photophysical Properties of NBN-Doped Polycyclic Aromatic Hydrocarbons: A Theoretical Study

2021 ◽  
Author(s):  
Yi Zeng ◽  
Junfang Yang ◽  
Xiaoyan Zheng
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Aromatic Hydrocarbons ◽  
Theoretical Study ◽  
Photophysical Properties ◽  
Structure Property ◽  
Vital Importance ◽  
Property Relationship ◽  
Structure Property Relationship ◽  
Polycyclic Aromatic ◽  
Boron Nitrogen

To realize the precise munipulation of the optoelectrical properties of boron–nitrogen (B–N) unit-doped Polycyclic aromatic hydrocarbons (PAHs), unraveling the structure-property relationship behind is of vital importance. In this work, we...

Precise molecular design for BN-modified polycyclic aromatic hydrocarbons toward mechanochromic materials

2020 ◽  
Vol 8 (42) ◽  
pp. 22023-22031
Author(s):  
Huanan Huang ◽  
Ying Zhou ◽  
Yawei Wang ◽  
Xiaohua Cao ◽  
Chuan Han ◽  
...  
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Aromatic Hydrocarbons ◽  
Smart Materials ◽  
Molecular Design ◽  
Molecular Level ◽  
Design Strategy ◽  
Material Base ◽  
Polycyclic Aromatic ◽  
Level Design ◽  
Boron Nitrogen

This paper reports on a novel molecular-level design strategy to achieve a novel MCL material base on boron and nitrogen aromatics. The introduction of boron nitrogen unit is the key to design the MCL smart materials.

scholarly journals Diversity-oriented synthesis of nanographenes enabled by dearomative annulative π-extension

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Wataru Matsuoka ◽  
Hideto Ito ◽  
David Sarlah ◽  
Kenichiro Itami
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Aromatic Hydrocarbons ◽  
Template Synthesis ◽  
Science And Technology ◽  
Synthetic Methods ◽  
Structure Property ◽  
Oriented Growth ◽  
Diversity Oriented Synthesis ◽  
Potential Applications ◽  
Polycyclic Aromatic

AbstractNanographenes and polycyclic aromatic hydrocarbons (PAHs) are among the most important classes of compounds, with potential applications in nearly all areas of science and technology. While the theoretically possible number of nanographene structures is extraordinary, most of these molecules remain synthetically out of reach due to a lack of programmable and diversity-oriented synthetic methods, and their potentially huge structure-property diversity has not been fully exploited. Herein we report a diversity-oriented, growth-from-template synthesis of nanographenes enabled by iterative annulative π-extension (APEX) reactions from small PAH starting materials. The developed dearomative annulative π-extension (DAPEX) reaction enables π-elongation at the less-reactive M-regions of PAHs, and is successfully combined with complementary APEX reactions that occur at K- and bay-regions to access a variety of previously untapped nanographenes.

scholarly journals Identification of Polycyclic Aromatic Hydrocarbons

1987 ◽  
Vol 120 ◽  
pp. 557-558
Author(s):  
A. Léger ◽  
L. D'Hendecourt
Keyword(s):  
Polycyclic Aromatic Hydrocarbons ◽  
Aromatic Hydrocarbons ◽  
Organic Molecules ◽  
Polycyclic Aromatic ◽  
Small Grains ◽  
Ir Emission ◽  
Graphitic Material

The nature of the Very Small Grains evidenced by K. Sellgren (1985) is discussed. Their stability suggests that they are graphitic material and specifically Polycyclic Aromatic Hydrocarbons (PAHs). The expected IR emission of a typical PAH, coronene, gives an impressive spectroscopic agreement with the five observed “Unidentified IR Emission Features”, leading to an unambiguous identification. Those PAHs are the most abundant organic molecules detected to this date (f ~ 10−5).

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