Article
Chemistry, Multidisciplinary
Michael P. Moghadasnia, Brian J. Eckstein, Gary J. Balaich, C. Michael McGuirk
Summary: By using density functional theory-based calculations, a high-fidelity and self-complementary halogen bonding moiety, 2-iodooxazole, was discovered. The installation of 2-iodooxazole on two geometrically complementary cores resulted in the formation of tectons 1,4-bis(2-iodooxazol-5-yl)benzene (BIOx) and 1,4-bis(2-iodooxazol-5-yl)-2,3,5,6-tetrafluorobenzene (FIOx). Single crystal X-ray diffraction studies showed that both BIOx and FIOx exhibit the necessary strength and geometry to assemble into crystalline, multi-dimensional halogen-bonded networks. By controlling the assembly conditions, one, two, or three-dimensional halogen-bonded networks can be deliberately formed. This work demonstrates that halogen-bonded networks can meet the standards set by hydrogen-bonded analogues through careful design and control.
CRYSTAL GROWTH & DESIGN
(2023)
Article
Chemistry, Multidisciplinary
Taylor A. Bramlett, Adam J. Matzger
Summary: This study experimentally determined the relative strength of halogen bonding interactions in solution by Raman spectroscopic observation of complexes formed from interacting iodobenzene-derived XB donors and pyridine XB acceptors. The evaluation of binding energy coupling with ALMO-EDA analysis revealed a prominent role for charge transfer interactions in halogen bonding energy contributions. Raman spectra accurately predicted stronger interactions within IPFB complexes than with IDNB complexes, despite IPFB having similar electrostatics to IDNB and containing a smaller sigma-hole.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Chemistry, Multidisciplinary
Subhendu Biswas, Anindita Das
Summary: The amalgamation of controlled polymer synthesis and supramolecular chemistry is crucial for generating modern-day emerging polymeric materials. Halogen bonding, with advantageous features like superior hydrophobicity, directionality, and polar solvent resistance, is highly desirable for constructing functional materials.
Article
Chemistry, Physical
Xinrui Miao, Zhengkai Cai, Jinxing Li, Liqian Liu, Juntian Wu, Bang Li, Lei Ying, Fabien Silly, Wenli Deng, Yong Cao
Summary: The self-assembled material stabilized by halogen bonding, m-BrTBE, forms uniform ball-like aggregates with high photoluminescence quantum yield, showing a more red-shifted emission compared to TBE. The enhanced AIE behavior is attributed to the important effect of meta-bromide substituents, promoting radiative processes and blocking nonradiative relaxation pathways.
Article
Chemistry, Multidisciplinary
Andrey S. S. Smirnov, Alexander S. S. Mikherdov, Anton V. V. Rozhkov, Rosa M. M. Gomila, Antonio Frontera, Vadim Yu. Kukushkin, Nadezhda A. A. Bokach
Summary: Co-crystallization of 1,4-diisocyanobenzene (1) and 1,4-diisocyanotetramethylbenzene (2) with halogen bond donors such as 1,4-diiodotetrafluorobenzene (1,4-FIB) and 4,4'-diiodoperfluorobiphenyl (4,4'-FIBP) resulted in the formation of co-crystals 1 . 1,4-FIB, 1 . 4,4'-FIBP, and 2 . 1,4-FIB. The solid-state structures showed 1D-supramolecular arrangements based on poorly explored I...C halogen bonding, and the use of tetraiodoethylene (TIE) resulted in a 3D-framework supramolecular architecture in the structure of 1 . TIE. DFT calculations indicated moderately strong I...C non-covalent interactions, and NBO analysis revealed relevant LP(C)->sigma* charge transfer effects in all co-crystals.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Polymer Science
Sunting Xuan, Xi Jiang, Nitash P. Balsara, Ronald N. Zuckermann
Summary: The research shows that through utilizing complementary molecular shapes, selective assembly between sequence-defined peptoids can be achieved. Peptoids with different overall molecular shapes were able to form crystalline nanosheets with the same lattice structure in aqueous solution.
Article
Chemistry, Multidisciplinary
Gizem Gumusgoz Celik, Burcu Dedeoglu, Ayse Gul Gurek, Yunus Zorlu, Mehmet Menaf Ayhan
Summary: Supramolecular synthesis using halogen bonding was employed to facilitate the co-crystallization of BODIPY structures with nitrogen-containing structures. Successful synthesis of BODIPY derivative co-crystals was achieved by increasing geometric accessibility of s holes of iodine. The crystal structures exhibited different architectures, driven mainly by electrostatic forces.
CRYSTAL GROWTH & DESIGN
(2023)
Article
Chemistry, Organic
Raffaella Papagna, Dana Kutzinski, Stefan M. Huber
Summary: In this study, recyclable polymer-bound halogen bonding catalysts were developed, which exhibited comparable catalytic activity to free halogen bond donors. This proof-of-principle research provides a foundation for the further development of sustainable halogen bonding organocatalysts.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zhuoer Wang, Aiyou Hao, Pengyao Xing
Summary: This study investigates how halogenation influences protein or peptide folding and self-assembly hierarchically using halogen bonding mediated self-assemblies on cyclodipeptide scaffolds. The results show that single-functionalized cyclodipeptides (Cyclo-GX) form homochiral helical nanotubes via consecutive X center dot center dot center dot O bonds independent of halogen kinds. In contrast, double-functionalized cyclodipeptides (Cyclo-XX) exhibit versatile self-assembly architectures depending on the para-substituents, leading to nanotubular, lamellar, and triple helical nanotubular structures. It is also found that halogen substitution affects molecular folding, packing, and chirality at hierarchical levels. Additionally, clusteroluminescence and circularly polarized luminescence with tunable handedness are achieved in the cyclodipeptides by controlling halogen substituents.
Article
Chemistry, Multidisciplinary
Wenhao Dong, Yan Zhang, Chenglin Yi, Julia J. Chang, Shunsheng Ye, Zhihong Nie
Summary: This study describes the reversible self-assembly of plasmonic nanoparticles capped with complementary copolymer ligands into colloidal molecules via halogen bonding interactions. The coordination number of the colloidal molecules is determined by the number ratio of complementary halogen groups on the interacting nanoparticles. The reversibility of the halogen bonds allows for controlling the formation and disassociation of the colloidal molecules and their optical properties. The engineered reversible nanostructures may have applications in sensing, catalysis, and optoelectronic devices.
Article
Biochemistry & Molecular Biology
Erin D. Speetzen, Chideraa I. Nwachukwu, Nathan P. Bowling, Eric Bosch
Summary: This study expands on previous research and combines the concepts of ditopic halogen bonding and π-stacking in cocrystallization. The experiments demonstrate the complementary interaction between electron donor-acceptor pairs through halogen bonding and π-complexation, with computations confirming the strength of π-stacking over halogen bonding and the cooperative effect between the two.
Review
Chemistry, Multidisciplinary
Pierangelo Metrangolo, Laura Canil, Antonio Abate, Giancarlo Terraneo, Gabriella Cavallo
Summary: Hybrid organic-inorganic halide perovskites have emerged as promising materials for next-generation solar cells due to their easy and low-cost production and unique optoelectronic properties. However, their practical implementation is hindered by their poor stability in air and moisture. Optimizing the chemical composition and exploiting non-covalent interactions can enhance the efficiency and stability of perovskite solar cells.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Xihuang Zheng, Min Ren, Huayang Wang, Huiying Wang, Zhen Geng, Jiangping Xu, Renhua Deng, Senbin Chen, Wolfgang H. Binder, Jintao Zhu
Summary: Halogen-bond driven assembly in emulsion droplets enables order-order phase transitions by forming donor-acceptor pairs, leading to various nanostructures. Tuning the content of halogen donor and choice of surfactant allows for tailored morphology transitions, creating mesoporous microparticles, disassembled nanodiscs, and superaggregates. These results will inspire further exploration of halogen bonding interactions in emulsion droplets and beyond.
Article
Chemistry, Multidisciplinary
Alica C. Keuper, Kevin Fengler, Florian Ostler, Tobias Danelzik, Dariusz G. Piekarski, Olga Garcia Mancheno
Summary: A new approach to achieve highly enantioselective halogen-bonding catalysis has been developed by designing fine-tuned halogen-halogen interactions. This strategy utilizes both the electron cloud and sigma-hole site of the substrate's halogen substituent to form a tight chiral complex, enabling controlled induction of high levels of chirality transfer. Remarkable enantioselectivities of up to 95:5 e.r. (90% ee) have been achieved in a model dearomatization reaction using tetrakis-iodotriazole multidentate anion-binding catalysts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Pascal Vermeeren, Lando P. Wolters, Gabor Paragi, Celia Fonseca Guerra
Summary: Cooperative properties of halogen bonds were investigated through computational experiments, showing that cyanogen halide and halocyanoacetylene chains exhibit additional stabilizing effects with increasing chain length, while 4-halobenzonitrile chains do not. This cooperativity can be attributed to charge transfer leading to charge separation within the sigma-electronic system.
Article
Chemistry, Physical
Alan Vanderkooy, Mark S. Taylor
FARADAY DISCUSSIONS
(2017)
Article
Polymer Science
Alan Vanderkooy, Philipp Pfefferkorn, Mark S. Taylor
Article
Chemistry, Physical
Alan Vanderkooy, Mark S. Taylor
FARADAY DISCUSSIONS
(2017)
Article
Nanoscience & Nanotechnology
Alan Vanderkooy, Yang Chen, Ferdinand Gonzaga, Michael A. Brook
ACS APPLIED MATERIALS & INTERFACES
(2011)
Article
Nanoscience & Nanotechnology
Alan Vanderkooy, Michael A. Brook
ACS APPLIED MATERIALS & INTERFACES
(2012)
Article
Chemistry, Multidisciplinary
Alan Vanderkooy, Arvind Kumar Gupta, Tamas Foldes, Sofia Lindblad, Andreas Orthaber, Imre Papai, Mate Erdelyi
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
