Incorporating Ester Functionality within a Solid-State [2 + 2] Cycloaddition Reaction Based Upon Halogen Bonding Interactions

2020 ◽  
Vol 20 (3) ◽  
pp. 1969-1974 ◽  
Author(s):  
Samantha J. Kruse ◽  
Eric Bosch ◽  
Fayeshun Brown ◽  
Ryan H. Groeneman
Keyword(s):  
Solid State ◽  
Cycloaddition Reaction ◽  
Halogen Bonding

Regioselective [2 + 2] cycloaddition reaction within a pair of polymorphic co-crystals based upon halogen bonding interactions

CrystEngComm ◽  
2019 ◽  
Vol 21 (43) ◽  
pp. 6671-6675 ◽  
Author(s):  
Eric Bosch ◽  
Samantha J. Kruse ◽  
Eric W. Reinheimer ◽  
Nigam P. Rath ◽  
Ryan H. Groeneman
Keyword(s):  
Solid State ◽  
Cycloaddition Reaction ◽  
Halogen Bonding

A pair of photoreactive polymorphic co-crystals that undergo a regioselective solid-state [2 + 2] cycloaddition reaction that yields exclusively the head-to-tail photoproduct is reported.

Role of π–π Stacking and Halogen Bonding by 1,4-Diiodoperchlorobenzene To Organize the Solid State To Achieve a [2 + 2] Cycloaddition Reaction

2019 ◽  
Vol 19 (6) ◽  
pp. 3092-3096 ◽  
Author(s):  
Eric Bosch ◽  
Samantha J. Kruse ◽  
Herman R. Krueger ◽  
Ryan H. Groeneman
Keyword(s):  
Solid State ◽  
Cycloaddition Reaction ◽  
Halogen Bonding ◽  
Π Stacking

Tuning the configuration of the flexible metal–alkene-framework affords pure cycloisomers in solid state photodimerization

2021 ◽  
Author(s):  
Yong Wang ◽  
Meng-Fan Wang ◽  
David James Young ◽  
Hua Zhu ◽  
Fei-Long Hu ◽  
...  
Keyword(s):  
Solid State ◽  
Cycloaddition Reaction ◽  
Guest Molecules ◽  
Flexible Metal

The bulkiness of the guest molecules influences the conformations of the ligand and the final outcomes of the cycloaddition reaction.

scholarly journals Zn(II) Heteroleptic Halide Complexes with 2-Halopyridines: Features of Halogen Bonding in Solid State

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3393
Author(s):  
Mikhail A. Vershinin ◽  
Marianna I. Rakhmanova ◽  
Alexander S. Novikov ◽  
Maxim N. Sokolov ◽  
Sergey A. Adonin
Keyword(s):  
Solid State ◽  
Quantum Yield ◽  
Crystal Packing ◽  
Halogen Bonding ◽  
Molecular Complexes ◽  
Substituted Pyridines ◽  
Halide Complexes

Reactions between Zn(II) dihalides and 2-halogen-substituted pyridines 2-XPy result in a series of heteroleptic molecular complexes [(2-XPy)2ZnY2] (Y = Cl, X = Cl (1), Br (2), I (3); Y = Br, X = Cl (4), Br (5), I (6), Y = I, X = Cl (7), Br (8), and I (9)). Moreover, 1–7 are isostructural (triclinic), while 8 and 9 are monoclinic. In all cases, halogen bonding plays an important role in formation of crystal packing. Moreover, 1–9 demonstrate luminescence in asolid state; for the best emitting complexes, quantum yield (QY) exceeds 21%.

An insight to the noncovalent interactions in two triamine based mononuclear iron(III) Schiff base complexes with special emphasis on the formation of Br•••π halogen bonding

CrystEngComm ◽  
2021 ◽  
Author(s):  
Shouvik Chattopadhyay ◽  
Tanmoy Basak ◽  
Antonio Frontera
Keyword(s):  
Schiff Base ◽  
Solid State ◽  
Noncovalent Interactions ◽  
Halogen Bonding ◽  
Schiff Base Complexes ◽  
X Ray ◽  
Mononuclear Iron

Two mononuclear iron(III) complexes, [FeL1Cl]∙CH3CN (1) and [FeL2(N3)] (2) {H2L1= N,N′-bis(5-chlorosalicylidene)diethylenetriamine and H2L2= N,N′-bis(5-bromosalicylidene)diethylenetriamine}, have been synthesized and characterized by X-ray crystallographic studies. In the solid state, there are strong...

scholarly journals Fluorinated azobenzenes as supramolecular halogen-bonding building blocks

2019 ◽  
Vol 15 ◽  
pp. 2013-2019 ◽  
Author(s):  
Esther Nieland ◽  
Oliver Weingart ◽  
Bernd M Schmidt
Keyword(s):  
Solid State ◽  
Dft Calculations ◽  
Visible Light ◽  
Half Life ◽  
Photophysical Properties ◽  
Bathochromic Shift ◽  
Halogen Bonding ◽  
Building Blocks ◽  
Partial Overlap

ortho-Fluoroazobenzenes are a remarkable example of bistable photoswitches, addressable by visible light. Symmetrical, highly fluorinated azobenzenes bearing an iodine substituent in para-position were shown to be suitable supramolecular building blocks both in solution and in the solid state in combination with neutral halogen bonding acceptors, such as lutidines. Therefore, we investigate the photochemistry of a series of azobenzene photoswitches. Upon introduction of iodoethynyl groups, the halogen bonding donor properties are significantly strengthened in solution. However, the bathochromic shift of the π→π* band leads to a partial overlap with the n→π* band, making it slightly more difficult to address. The introduction of iodine substituents is furthermore accompanied with a diminishing thermal half-life. A series of three azobenzenes with different halogen bonding donor properties are discussed in relation to their changing photophysical properties, rationalized by DFT calculations.

scholarly journals 1,1,4,4-Tetracyanobutadiene-Functionalized Anthracenes: Regioselectivity of Cycloadditions in the Synthesis of Small Near-IR Dyes

2020 ◽  
Author(s):  
Clotilde Philippe ◽  
Anh Thy Bui ◽  
Sabrinah Batsongo-Boulingui ◽  
ziemowit Pokladek ◽  
Katarzyna Matczyszyn ◽  
...  
Keyword(s):  
Solid State ◽  
Dft Calculations ◽  
Cycloaddition Reaction ◽  
Diels Alder ◽  
Reaction Sequence ◽  
Near Ir

<p>Two small 1,1,4,4-tetracyanobutadiene-functionalized chromophores were obtained by careful leverage of the regioselectivity of the cycloaddition reaction of tetracyanoethylene with anthracene-ynamide derivatives, inducing either a [2+2] or a [4+2] Diels–Alder process. DFT calculations unraveled the mechanism of the [2+2] cycloaddition-retroelectrocyclization reaction sequence with ynamides and elucidated the differing mechanisms in the two substrates. The synthesized dyes presented panchromatic absorption extending into the near-IR, and far-red/near-IR photoluminescence in the solid-state up to 1550 nm.</p>

σ-Hole halogen bonding interactions in a mixed valence cobalt(iii/ii) complex and anti-electrostatic hydrogen bonding interaction in a cobalt(iii) complex: a theoretical insight

CrystEngComm ◽  
2018 ◽  
Vol 20 (45) ◽  
pp. 7281-7292 ◽  
Author(s):  
Kousik Ghosh ◽  
Klaus Harms ◽  
Antonio Bauzá ◽  
Antonio Frontera ◽  
Shouvik Chattopadhyay
Keyword(s):  
Hydrogen Bonding ◽  
Solid State ◽  
Dft Calculations ◽  
Mixed Valence ◽  
Halogen Bonding ◽  
Supramolecular Interactions ◽  
Hydrogen Bonding Interaction ◽  
Bonding Interaction ◽  
Solid State Structures ◽  
Theoretical Insight

Supramolecular interactions in the solid state structures of a mixed valence cobalt(ii/iii) complex and a cobalt(iii) complex have been studied using DFT calculations.

scholarly journals Halogen bonding, chalcogen bonding, pnictogen bonding, tetrel bonding: origins, current status and discussion

2017 ◽  
Vol 203 ◽  
pp. 485-507 ◽  
Author(s):  
Lee Brammer
Keyword(s):  
Solid State ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Main Group ◽  
Solution Phase ◽  
Current Status ◽  
Solid State Chemistry ◽  
Main Group Elements ◽  
Past Work

The role of the closing lecture in a Faraday Discussion is to summarise the contributions made to the Discussion over the course of the meeting and in so doing capture the main themes that have arisen. This article is based upon my Closing Remarks Lecture at the 203rdFaraday Discussion meeting on Halogen Bonding in Supramolecular and Solid State Chemistry, held in Ottawa, Canada, on 10–12thJuly, 2017. The Discussion included papers on fundamentals and applications of halogen bonding in the solid state and solution phase. Analogous interactions involving main group elements outside group 17 were also examined. In the closing lecture and in this article these contributions have been grouped into the four themes: (a) fundamentals, (b) beyond the halogen bond, (c) characterisation, and (d) applications. The lecture and paper also include a short reflection on past work that has a bearing on the Discussion.

Halogen bonding between entirely negative fluorine atoms? Evidence from the crystal packing of some gold(i) and gold(iii) complexes with extensively fluorinated m-terphenyl ligands and triphenylphosphane

CrystEngComm ◽  
2020 ◽  
Vol 22 (48) ◽  
pp. 8285-8289
Author(s):  
Alexandru Sava ◽  
Krisztina T. Kegyes ◽  
Bianca T. Popuş ◽  
Bernadette C. Dan ◽  
Cristian Silvestru ◽  
...  
Keyword(s):  
Solid State ◽  
Intermolecular Interactions ◽  
Crystal Packing ◽  
Halogen Bonding ◽  
Terphenyl Ligands

Intermolecular interactions between fluorine atoms, analogous to halogen bonding, are able to drive the solid-state arrangement of molecules.

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