scholarly journals Easier to Twist than Bend: The Scope of the Bridge Formation Approach to Naphthalenophane Synthesis

2020 ◽  
Vol 02 (04) ◽  
pp. 323-329
Author(s):  
Anjan Bedi ◽  
Linda J. W. Shimon ◽  
Benny Bogoslavsky ◽  
Ori Gidron

Twisting anthracene and higher acenes can alter their optical, magnetic, and electronic properties. To test the effect of twisting on the lower homologue, naphthalene, we synthesized tethered naphthalenophanes bearing alkyl bridges. Both X-ray structure and DFT calculations show that hexyl and butyl bridges induce a 6° and 12° end-to-end twist on the naphthalene unit, respectively. Attempts to increase the twisting further using shorter tethers resulted in an elimination product. Enantiomerically pure naphthalenophanes display strong chiroptical properties, which intensify with increasing twist. Attempts to induce bending, rather than twisting, using the same synthetic methodology, resulted in intermolecular dimerization, yielding macrocyclic naphthalenes. This work highlights the importance of steric hindrance in the synthesis of curved cyclophanes using the bridge formation approach.

2004 ◽  
Vol 14 (6) ◽  
pp. 250-253 ◽  
Author(s):  
Markus Albrecht ◽  
Ingo Janser ◽  
Jörg Fleischhauer ◽  
Yuekui Wang ◽  
Gerhard Raabe ◽  
...  

2008 ◽  
Vol 73 (6-7) ◽  
pp. 786-794 ◽  
Author(s):  
B. Andes Hess ◽  
Lidia Smentek

A conformational analysis of squalene encapsulated in squalene-hopene cyclase has been performed based on Schulz's X-ray structure and our DFT calculations. Based on this analysis it is concluded that the formation of rings A-D in the cyclization of squalene are likely to be a concerted but highly asynchronous reaction.


2021 ◽  
Author(s):  
Anna Agnieszka Hoser ◽  
Marcin Sztylko ◽  
Damian Trzybiński ◽  
Anders Østergaard Madsen

A framework for estimation of thermodynamic properties for molecular crystals via refinement of frequencies from DFT calculations against X-ray diffraction data is presented. The framework provides an efficient approach to...


Small ◽  
2021 ◽  
pp. 2005162
Author(s):  
Ziyi Chen ◽  
Andrew G. Walsh ◽  
Xiao Wei ◽  
Manzhou Zhu ◽  
Peng Zhang

2019 ◽  
Vol 23 (11n12) ◽  
pp. 1346-1354 ◽  
Author(s):  
Danielle Laurencin ◽  
Pascal G. Yot ◽  
Christel Gervais ◽  
Yannick Guari ◽  
Sébastien Clément ◽  
...  

Porphyrin nanorods were prepared by ion-association between free-base meso 5,10,15,20-tetrakis-(4-[Formula: see text]-methylpyridinium)porphyrin cations and tetraphenylborate anions. The nanorods have variable lengths (up to a few micrometers long) and diameters ([Formula: see text]50–500 nm). Their structure at the molecular level was elucidated by combining multinuclear solid state NMR spectroscopy, synchrotron X-ray powder diffraction and DFT calculations.


2000 ◽  
Vol 19 (26) ◽  
pp. 5589-5596 ◽  
Author(s):  
Michael Bühl ◽  
Mikael Håkansson ◽  
Amir H. Mahmoudkhani ◽  
Lars Öhrström
Keyword(s):  

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