20799-74-0Relevant academic research and scientific papers
Strong and Selective Halide Anion Binding by Neutral Halogen-Bonding [2]Rotaxanes in Wet Organic Solvents
Lim, Jason Y. C.,Bunchuay, Thanthapatra,Beer, Paul D.
, p. 4700 - 4707 (2017)
The design and construction of neutral interlocked host molecules for anion recognition are rare. Using an active-metal template approach, the preparation of a family of neutral halogen bonding (XB) rotaxanes containing two, three and four iodotriazole groups integrated into the macrocycle and axle components is achieved. In spite of the interlocked hosts’ neutrality, such rotaxane systems are capable of binding halide anions strongly and selectively in wet organic solvent mixtures. Importantly, halide-binding strength and selectivity can be modulated by varying the number and position of the halogen bond donor iodotriazole groups within the interlocked cavity; the rotaxane containing the largest number of halogen bond donor groups exhibits the highest halide anion-binding affinities. By varying the percentage of water content in the solvent, neutral XB donor-mediated anion-binding strength is also demonstrated to be highly sensitive to solvent polarity.
A new halogen bonding 1,2-iodo-triazolium-triazole benzene motif for anion recognition
Beer, Paul D.,Bunchuay, Thanthapatra,Docker, Andrew,White, Nicholas G.
, (2021/09/28)
The synthesis of a series of halogen bonding (XB) acyclic anion receptors based on a novel 1,2-iodo-triazolium-triazole benzene motif is reported. A combination of one- and two-dimensional 1H and 19F NMR spectroscopic techniques eluc
Gold-catalyzed hydroarylating cyclization of 1,2-Bis(2-iodoethynyl)benzenes
N?sel, Pascal,Müller, Vanessa,Mader, Steffen,Moghimi, Setareh,Rudolph, Matthias,Braun, Ingo,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 500 - 506 (2015/03/05)
1,5-Diynes bearing halogen-substituted alkynes were synthesized and converted in the presence of a gold catalyst. In contrast to the corresponding hydroarylating aromatization reaction with terminal alkynes, a totally different reaction mode was observed.
Serendipity and the search for short N - I halogen bonds
Bosch, Eric
, p. 126 - 130 (2014/01/17)
The X-ray structure of the complex formed between N,N-dimethylaminopyridine (DMAP) and 1,2-bis(iodoethynyl)benzene is reported. The N - I halogen bond lengths are 2.654 and 2.662 A, approximately 75% of the sum of the van der Waals radii. On the basis of literature precedent and electrostatic potential calculations, a series of fluorosubstituted iodophenylacetylenes were prepared and individually complexed with dimethylaminopyridine in a search for shorter halogen bonds. A N - I halogen bond distance of 2.680 A was observed in the DMAP complex with 3,5-difluoro(iodoethynyl)benzene, and halogen bond distances of 2.622, 2.676, 2.700, and 2.705 A were observed in the complex of 4-fluoro(iodoethynyl)benzene with DMAP. These N - I bond distances range from 74.3 to 76.6% of the sum of the van der Waals radii.
Fusing triazoles: Toward extending aromaticity
Juricek, Michal,Stout, Kathleen,Kouwer, Paul H. J.,Rowan, Alan E.
supporting information; experimental part, p. 3494 - 3497 (2011/09/14)
A novel method to extend aromaticity by one benzene and two triazole rings was developed and optimized. This two-step route employs the copper-catalyzed azide-haloalkyne cycloaddition reaction of an ortho-bis(iodoacetylene) system and the subsequent intra
The trisubstituted-triazole approach to extended functional naphthalocyanines
Jurí?ek, Michal,Stout, Kathleen,Kouwer, Paul H.J.,Rowan, Alan E.
experimental part, p. 898 - 907 (2012/03/26)
Recently, a novel modular approach to octatriazole-derived phthalocyanines (Pcs; 1) was developed and optimized in our group; herein, the pool of the functional Pc materials was expanded for an additional candidate (2), a fused derivative of 1. Compared w
