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Imide-based trezimide and tennimide macrocycles.

Gallagher, John F. and Mocilac, Pavle (2013) Imide-based trezimide and tennimide macrocycles. In: European Crystallographic Association Meeting, 25-29 Aug 2013, University of Warwick, U.K..

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Abstract

Reaction of isophthaloyl dichloride (I) with 2-aminopyridine or 2-aminopyrimidine (O, 26O) provides a facile entry into a new class of imide-based ‘3+3’ macrocyclic trimer (IO)3, (26IO)3 (as trezimides), together with the known tetramer (IO)4, (26IO)4 (tennimide) scaffold.1-5 Trezimides can adopt two asymmetric conformations, isolated as (P) in (IO)3 and (R) in (26IO)3.2,4 The tennimide (26IO)4 structure exhibits three discrete conformations as cc/oc/oo, highlighting subtle geometric changes with the tennimide channel (pore) open (o) and/or closed (c). Macrocycle formation (competing with oligomer/polymer formation) relies on the ortho-pyr(im)idine N functionality and imide hinge ('COCO' twist) with the inherent flexibility of the isophthaloyl groups (Figures 1-5).

Item Type:Conference or Workshop Item (Poster)
Event Type:Conference
Refereed:Yes
Additional Information:Cambridge Structural Database (CSD) information on the five brominated trezimides and tennimides: CCDC reference codes 930689 to 930693. Copies available, e-mail:deposit@ccdc.cam.ac.uk). Related macrocycles are available for viewing at a website: http://www.youtube.com/user/tennimidandtrezimid
Uncontrolled Keywords:Macrocycles; Molecular cavity; Pyridine; Pyrimidine; Imide; Bromine; Trezimide; Tennimide; Halogen bonding; Hydrogen bonding
Subjects:Physical Sciences > Organic chemistry
Physical Sciences > Chemistry
Physical Sciences > Crystallography
DCU Faculties and Centres:DCU Faculties and Schools > Faculty of Science and Health > School of Chemical Sciences
Use License:This item is licensed under a Creative Commons Attribution-NonCommercial-Share Alike 3.0 License. View License
Funders:PRTLI T3
ID Code:19698
Deposited On:17 Dec 2013 15:56 by John Gallagher. Last Modified 17 Dec 2013 15:56

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