Semiconductor Cocrystals Based on Boron: Generated Electrical Response with π-Rich Aromatic Molecules

Ray, Kamal K.; Campillo‐Alvarado, Gonzalo; Morales‐Rojas, Hugo; Höpfl, Herbert; MacGillivray, Leonard R.; Tivanski, Alexei V.

doi:10.1021/acs.cgd.9b00953

Cited by 22 publications

(25 citation statements)

References 46 publications

(71 reference statements)

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“…Interestingly, in ( 4 ) 2 DMBiPy⊃TTF all TTF complexes are oriented in the same way along the c ‐axis, providing a permanent polarity order to the crystal structure. The aforementioned features in ( 4 ) 2 DMBiPy⊃TTF must facilitate charge carrier mobility ( i. e ., semiconducting behavior) in similar fashion to a formerly studied TTF cocrystal with ( 7 ) 2 BiPy as host (where 7 =2,4‐difluorophenyl‐B‐catecholate) …”

Section: Resultsmentioning

confidence: 99%

Boron–Nitrogen Double Tweezers Comprising Arylboronic Esters and Diamines: Self‐Assembly in Solution and Adaptability as Hosts for Aromatic Guests in the Solid State

2020

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The thermodynamic stability of 1 : 1 and 2 : 1 boron–nitrogen (B←N) adducts formed between aromatic boronic esters with mono‐ and diamines was studied in solution by NMR and UV‐vis spectroscopy with association energies (ΔG°) ranging from −11 to −28 kJ mol−1. The effect of different substituents in the boronic ester, the nature of the diamine linker, and the effect of the solvent was explored. Stable 2 : 1 B←N adducts with diamines such as 1,3‐diaminopropane were produced in solutions of hydrogen‐bonding acceptor solvents (acetonitrile and ethyl acetate), which can be isolated in the solid state as crystalline solvates, whereas the use of noncoordinating solvents such as 1,2‐dichloroethane afforded mainly 1 : 1 B←N adducts. In suitable combinations, aromatic bis‐pyridyl diamines produced stable 2 : 1 B←N adducts that were isolated either as solvent‐free solids, solvates, or cocrystals. In these crystalline forms, double‐tweezer hosts were observed with an exceptional syn/anti conformational guest‐adaptability driven by simultaneous donor‐acceptor and C−H⋅⋅⋅π interactions in the tweezer cavities, resembling preorganized covalent tweezer hosts. Interestingly, cocrystals with electron‐rich guests such as tetrathiafulvalene and pyrene showed non‐centrosymmetric crystal lattices with infinite π‐stacked donor–acceptor columns.

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Section: Resultsmentioning

confidence: 99%

Boron–Nitrogen Double Tweezers Comprising Arylboronic Esters and Diamines: Self‐Assembly in Solution and Adaptability as Hosts for Aromatic Guests in the Solid State

2020

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“…In previous publications, the H-bonding between pyridine derivatives and organoboronic acids was employed for various research purposes − but was never used to prepare soft materials such as LMOGs. Especially, in those works, single-crystal diffraction analysis was used to identify intramolecular interactions, which was probably due to the interaction modes with quantitatively precise ratios between pyridine derivatives and organoboronic acids. , Therefore, crystals of these supramolecular aggregates can be obtained more easily.…”

Section: Resultsmentioning

confidence: 99%

Fabricating Soft Fluorescent Materials by a Supramolecular Method and a Cost-Effective Approach to Effectively Sense Amine Vapors during Fish Spoilage

Zhang

Zhao

Zhang

et al. 2021

Ind. Eng. Chem. Res.

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In this paper, we present a supramolecular method to fabricate soft fluorescent materials by simply grinding aggregation-induced emission (AIE) luminogens of TPA-Py with phenylboronic acid (PhBA), which proves the general research concept used to design fluorescent materials with tunable emission colors. The mechanistic study confirms that H-bonding plays a key role in gel formation and the smart responsive behavior to external stimuli (such as amine vapors and temperature changes). Thus, this result endows the fluorescent materials with the ability to detect amine vapors during fish spoilage. In addition, copolymerization and coprecipitation are consecutively performed to prepare highly cost-effective, conveniently storable, and safe to handle fluorescence spheres (named Fluo-Spheres), which can be employed as ultrasensors to monitor food safety in a noncontact mode.

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“…The adaptability of the host towards guests of different size and electronic properties has enabled the formation separation of materials for separation of petrochemicals 31 and organic semiconductors (Figure 5). 27 Motivated by the above observations, we turned to make use of the B←N interaction to facilitate reactivity in the solid state. Our strategy involved the combination of 4stilbazole (4-sbz) with phenylboronic acid catechol ester (be).…”

Section: Boronic Esters As Templates For [2+2]-photocycloadditions In the Solid Statementioning

confidence: 99%

Opportunities Using Boron to Direct Reactivity in the Organic Solid State

Campillo‐Alvarado

MacGillivray

2020

Synlett

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This Account describes work by our research group that highlights opportunities to utilize organoboron molecules to direct chemical reactivity in the organic solid state. Specifically, we convey a previously unexplored use of hydrogen bonding of boronic acids and boron coordination in boronic esters to achieve [2+2]-photocycloadditions in crystalline solids. Organoboron molecules act as templates or ‘shepherds’ to organize alkenes in a suitable geometry to undergo regio- and stereoselective [2+2]-photocycloadditions in quantitative yields. We also provide a selection of publications that served as an inspiration for our strategies and offer challenges and opportunities for future developments of boron in the field of materials and solid-state chemistry.1 Introduction1.1 Template Strategy for [2+2]-Photocycloadditions in the Solid State2 Boronic Acids as Templates for [2+2]-Photocycloadditions in the Solid State2.1 Supramolecular Catalysis of [2+2]-Photocycloadditions in the Solid State Using Boronic Acids3 Boronic Esters as Templates for [2+2]-Photocycloadditions in the Solid State3.1 Application of Photoproducts: Separation of Thiophene from Benzene through Crystallization3.2 Crystal Reactivity of B←N-Bonded Adducts: The Case of Styrylthiophenes4 Conclusions and Perspectives

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Semiconductor Cocrystals Based on Boron: Generated Electrical Response with π-Rich Aromatic Molecules

Cited by 22 publications

References 46 publications

Boron–Nitrogen Double Tweezers Comprising Arylboronic Esters and Diamines: Self‐Assembly in Solution and Adaptability as Hosts for Aromatic Guests in the Solid State

Boron–Nitrogen Double Tweezers Comprising Arylboronic Esters and Diamines: Self‐Assembly in Solution and Adaptability as Hosts for Aromatic Guests in the Solid State

Fabricating Soft Fluorescent Materials by a Supramolecular Method and a Cost-Effective Approach to Effectively Sense Amine Vapors during Fish Spoilage

Opportunities Using Boron to Direct Reactivity in the Organic Solid State

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