Organic Synthesis in the Solid State via Hydrogen-Bond-Driven Self-Assembly

2008 ◽  
Vol 73 (9) ◽  
pp. 3311-3317 ◽  
Author(s):  
Leonard R. MacGillivray
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Organic Synthesis ◽  
Self Assembly

scholarly journals ‘Frustrated’ hydrogen bond mediated amphiphile self-assembly – a solid state study

CrystEngComm ◽  
2016 ◽  
Vol 18 (37) ◽  
pp. 7021-7028 ◽  
Author(s):  
Laura R. Blackholly ◽  
Helena J. Shepherd ◽  
Jennifer R. Hiscock
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Self Assembly ◽  
Hydrogen Bond Donor ◽  
System P ◽  
State Study ◽  
Counter Cation ◽  
Self Assembled ◽  
Hydrogen Bonded

The effects of hydrogen bond donor acidity and counter cation within a ‘frustrated’ self-assembled, hydrogen bonded system.

scholarly journals Precision Nanotube Mimics via Self-Assembly of Programmed Carbon Nanohoops

2019 ◽  
Author(s):  
Jeff M. Van Raden ◽  
Erik Leonhardt ◽  
Lev N. Zakharov ◽  
Andrés Pérez-Guardiola ◽  
Angel Jose Perez Jimenez ◽  
...  
Keyword(s):  
Carbon Nanotubes ◽  
Solid State ◽  
Organic Synthesis ◽  
Self Assembly ◽  
Carbon Nanomaterials ◽  
Weak Interactions ◽  
The Self ◽  
X Ray Crystallography ◽  
Access Structures ◽  
Potential Applications

The scalable production of homogenous, uniform carbon nanomaterials represents a key synthetic challenge for contemporary organic synthesis as nearly all current fabrication methods provide heterogenous mixtures of various carbonized products. For carbon nanotubes (CNTs) in particular, the inability to access structures with specific diameters or chiralities severely limits their potential applications. Here, we present a general approach to access solid-state CNT mimic structures via the self-assembly of fluorinated nanohoops, which can be synthesized in a scalable, size-selective fashion. X-ray crystallography reveals that these CNT mimics exhibit uniform channel diameters that are precisely defined by the diameter of their nanohoop constituents, which self-assemble in a tubular fashion via a combination of arene-pefluoroarene and C—H---F interactions. The nanotube-like assembly of these systems results in capabilities such as linear guest alignment and permanently accessible channels, both of which are observed in CNTs but not in the analogous all-hydrocarbon nanohoop systems. Calculations suggest that the organofluorine interactions observed in the crystal structure are indeed critical in the self-assembly and robustness of the CNT mimic systems. This work establishes the self-assembly of carbon nanohoops via weak interactions as an attractive means to generate solid-state materials that mimic carbon nanotubes, importantly with the unparalleled tunability enabled by organic synthesis. <br>

Hydrogen-Bond-Mediated Self-Assembly of 26-Membered Diaza Tetraester Crowns of 3,5-Disubstituted 1H-Pyrazole. Dimerization Study in the Solid State and in CDCl3Solution

2011 ◽  
Vol 76 (20) ◽  
pp. 8223-8231 ◽  
Author(s):  
Felipe Reviriego ◽  
Pilar Navarro ◽  
Vicente J. Arán ◽  
Maria Luisa Jimeno ◽  
Enrique García-España ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Self Assembly

scholarly journals Precision Nanotube Mimics via Self-Assembly of Programmed Carbon Nanohoops

2019 ◽  
Author(s):  
Jeff M. Van Raden ◽  
Erik Leonhardt ◽  
Lev N. Zakharov ◽  
Andrés Pérez-Guardiola ◽  
Angel Jose Perez Jimenez ◽  
...  
Keyword(s):  
Carbon Nanotubes ◽  
Solid State ◽  
Organic Synthesis ◽  
Self Assembly ◽  
Carbon Nanomaterials ◽  
Weak Interactions ◽  
The Self ◽  
X Ray Crystallography ◽  
Access Structures ◽  
Potential Applications

The scalable production of homogenous, uniform carbon nanomaterials represents a key synthetic challenge for contemporary organic synthesis as nearly all current fabrication methods provide heterogenous mixtures of various carbonized products. For carbon nanotubes (CNTs) in particular, the inability to access structures with specific diameters or chiralities severely limits their potential applications. Here, we present a general approach to access solid-state CNT mimic structures via the self-assembly of fluorinated nanohoops, which can be synthesized in a scalable, size-selective fashion. X-ray crystallography reveals that these CNT mimics exhibit uniform channel diameters that are precisely defined by the diameter of their nanohoop constituents, which self-assemble in a tubular fashion via a combination of arene-pefluoroarene and C—H---F interactions. The nanotube-like assembly of these systems results in capabilities such as linear guest alignment and permanently accessible channels, both of which are observed in CNTs but not in the analogous all-hydrocarbon nanohoop systems. Calculations suggest that the organofluorine interactions observed in the crystal structure are indeed critical in the self-assembly and robustness of the CNT mimic systems. This work establishes the self-assembly of carbon nanohoops via weak interactions as an attractive means to generate solid-state materials that mimic carbon nanotubes, importantly with the unparalleled tunability enabled by organic synthesis. <br>

scholarly journals Hydrogen Bonds and Self-Assembly to Direct Reactivity in the Solid State

2014 ◽  
Vol 70 (a1) ◽  
pp. C528-C528
Author(s):  
Leonard MacGillivray
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Self Assembly ◽  
Organic Molecules ◽  
Chemical Reactivity ◽  
Unique Form ◽  
Organic Solid ◽  
Control Chemical ◽  
Complex Organic ◽  
General Method

In this presentation, we will describe our efforts to develop a general method to control chemical reactivity in the organic solid state. We use the method to provide access to complex organic molecules such as ladderanes and cyclophanes. In our method, we exploit hydrogen-bond-directed self-assembly with the use of small-molecule templates to assemble and preorganize olefins for intermolecular [2+2] photodimerizations. The templates assemble the olefins within discrete supramolecular assemblies for single and multiple photoreactions. By assembling the olefins within discrete assemblies, we overcome problems of long-range packing that have frustrated previous attempts to control the dimerization. We will also demonstrate how the approach provides a unique form of supamolecular catalysis that exploits fundamentals of mechanochemistry.

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