scholarly journals Mechanochemical Transformation of Planar Polyarene to Curved Fused-Ring System: Solid-Phase Synthesis of Corannulene

2021 ◽  
Author(s):  
Yong Teoh ◽  
Gabor Báti ◽  
Felipe Garcia ◽  
Mihaiela C. Stuparu
Keyword(s):  
Gas Phase ◽  
Solid Phase Synthesis ◽  
Molecular Level ◽  
Solid Phase ◽  
Reaction Times ◽  
Ambient Conditions ◽  
Phase Synthesis ◽  
Mechanochemical Transformation ◽  
Fused Ring ◽  
Fused Ring System

This work demonstrates that mechanochemical forces can successfully transform a planar<br>polyarene into a curved geometry by creating new C-C bonds along the rim of the molecular structure.<br>In doing so, mechanochemistry does not require inert conditions or organic solvents and provide<br>better yields within shorter reaction times. This is illustrated in a 15-minute synthesis of corannulene,<br>a fragment of fullerene C60, in 66% yield through ball milling of planar tetrabromomethylfluoranthene<br>precursor under ambient conditions. Traditional solution and gas-phase synthetic pathways do not<br>compete with the practicality and efficiency offered by the mechanochemical synthesis, which now<br>opens up a new reaction space for inducing curvature at a molecular level.

scholarly journals Mechanochemical Transformation of Planar Polyarene to Curved Fused-Ring System: Solid-Phase Synthesis of Corannulene

2021 ◽  
Author(s):  
Yong Teoh ◽  
Gabor Báti ◽  
Felipe Garcia ◽  
Mihaiela C. Stuparu
Keyword(s):  
Gas Phase ◽  
Solid Phase Synthesis ◽  
Molecular Level ◽  
Solid Phase ◽  
Reaction Times ◽  
Ambient Conditions ◽  
Phase Synthesis ◽  
Mechanochemical Transformation ◽  
Fused Ring ◽  
Fused Ring System

This work demonstrates that mechanochemical forces can successfully transform a planar<br>polyarene into a curved geometry by creating new C-C bonds along the rim of the molecular structure.<br>In doing so, mechanochemistry does not require inert conditions or organic solvents and provide<br>better yields within shorter reaction times. This is illustrated in a 15-minute synthesis of corannulene,<br>a fragment of fullerene C60, in 66% yield through ball milling of planar tetrabromomethylfluoranthene<br>precursor under ambient conditions. Traditional solution and gas-phase synthetic pathways do not<br>compete with the practicality and efficiency offered by the mechanochemical synthesis, which now<br>opens up a new reaction space for inducing curvature at a molecular level.

scholarly journals Mechanochemical transformation of planar polyarenes to curved fused-ring systems

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Teoh Yong ◽  
Gábor Báti ◽  
Felipe García ◽  
Mihaiela C. Stuparu
Keyword(s):  
Molecular Structure ◽  
Gas Phase ◽  
Mechanochemical Synthesis ◽  
Molecular Level ◽  
Reaction Times ◽  
Ambient Conditions ◽  
Aromatic Molecules ◽  
Planar Structures ◽  
Mechanochemical Transformation ◽  
Fused Ring

AbstractThe transformation of planar aromatic molecules into π-extended non-planar structures is a challenging task and has not been realized by mechanochemistry before. Here we report that mechanochemical forces can successfully transform a planar polyarene into a curved geometry by creating new C-C bonds along the rim of the molecular structure. In doing so, mechanochemistry does not require inert conditions or organic solvents and provide better yields within shorter reaction times. This is illustrated in a 20-minute synthesis of corannulene, a fragment of fullerene C60, in 66% yield through ball milling of planar tetrabromomethylfluoranthene precursor under ambient conditions. Traditional solution and gas-phase synthetic pathways do not compete with the practicality and efficiency offered by the mechanochemical synthesis, which now opens up a new reaction space for inducing curvature at a molecular level.

Microwave assisted solid-phase synthesis of substituted tetraazaporphyrins and a phthalocyanine-peptide conjugate

2010 ◽  
Vol 14 (10) ◽  
pp. 891-903 ◽  
Author(s):  
Mercy Mudyiwa ◽  
Margaret W. Ndinguri ◽  
Steven A. Soper ◽  
Robert P. Hammer
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Synthesis Method ◽  
Reaction Times ◽  
Solid Support ◽  
Phase Synthesis ◽  
Covalently Bonded ◽  
Poly Ethylene ◽  
High Degree ◽  
Acid Labile

Various asymmetrically substituted phthalocyanines (Pcs) and porphyrazines (Pzs) have been synthesized in good yields using a solid-phase synthesis method with a poly(ethylene glycol) (PEG) resin attached to an indole linker as the solid support. These compounds are formed by cross condensation of maleonitrile or phthalonitrile with another phthalonitrile covalently bonded to the solid support with an amino linking group. The polymer bound Pc or Pz is separated by filtration, and washing the symmetrical Pc or Pz by-product. The amine Pc -appended to polyethylene glycol resin is further reacted to yield azide whilst still on the solid support. Cleavage of the Pc or Pz off the solid support results in 3:1 asymmetric Pz or Pz with high degree of purity, requiring minimal further purification. The use of hydrophilic PEG-based resin allows the symmetrical compound to be removed completely by washing whereas the acid labile indole linker makes it easier to cleave the product under mild conditions. The conjugation abilities of these compounds have been demonstrated by the successful conjugation of one of the azide Pcs with a peptide elaborated with an alkyne function. Use of microwave for the synthesis of these compounds results in shorter reaction times, higher yields and higher degree of purity.

Carbogenic π−Conjugated Domains as the Origin of Afterglow Emission in Carbon Dot−Based Organic Composite films

2021 ◽  
Author(s):  
Lu Zhai ◽  
Xiaoming Ren ◽  
Qiang Xu
Keyword(s):  
Organic Materials ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Composite Films ◽  
Ambient Conditions ◽  
Phase Synthesis ◽  
Carbon Dot ◽  
Synthesis Approach

The development of carbon dot (CD)-based pure organic materials displaying afterglow emission under ambient conditions with readily tunable emissions is highly desired. Herein, a facile solid-phase synthesis approach at ambient...

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