N-Methylated 1,8-Diaminonaphthalenes as Bifunctional Nucleo­philes in Reactions with α,ω-Dihalogenoalkanes: A Facile Route to Heterocyclic and Double Proton Sponges

The reaction of 1-dimethylamino-8-(methylamino)naphthalene with 1,3-dibromopropane chemoselectively leads to the product of N,N′-heterocyclization, while in the case of 1,4-dibromobutane and 1,2-bis(bromomethyl)benzene the process results in heterocyclization onto the same nitrogen atom with the formation of previously unknown 1-dimethylamino-8-pyrrolidino- and 1-dimethylamino-8-isoindolino-naphthalenes. The same reactions conducted without adding any auxiliary base lead to the formation of N,N′-linked double proton sponges as a new type of polynitrogen organic receptor. Proceeding as a sequence of quaternization–demethylation–cyclization steps, this heterocyclization process can also be used to construct six-membered rings (piperidino, morpholino), albeit in lower yields. The ability of 1,2-dibromoethane to brominate N-alkylated 1,8-diaminonaphthalenes is also described. It is shown for the first time that a commercially available 1,8-bis(dimethylamino)naphthalene (DMAN) can be used as a starting material in a heterocyclization reaction, which via a one-pot approach and in a short time can be converted into 1,5-dimethylnaphtho[1,8-bc]-1,5-diazacyclooctane or 1-dimethylamino-8-(pyrrolidin-1-yl)naphthalene.

Introducing Selectivity on Carbonaceous Material: Removing Noble Salts, Au3+, and Ag+ from Aqueous Media by Nanodiamonds Functionalized with Squaramides

Nanodiamonds coated with dopamine−squaramide compounds have been prepared by a calcination/esterification synthetic process, which improves the efficiency of this carbonaceous material with respect to non-functionalized nanodiamonds. The modified nanodiamonds show excellent selective coordination of Ag+ and Au3+ cations in a Cd2+, Co2+, Cr3+, Cu2+, Pb2+, and Zn2+ mixture in water. The coordination capacity of the carbonyl squaramide groups with the silver and gold cation is based on purely electrostatic cation−dipole interactions. Overall, it is demonstrated that the conjunction between the nanodiamonds and the organic receptor improves the selectivity of the material toward noble cations.

Organic “receptor” fully covered few-layer organic–metal chalcogenides for high-performance chemiresistive gas sensing at room temperature

2D organic–metal chalcogenides (OMCs) were developed as a new type of material for high-performance RT gas sensing.

Thinking outside the “Blue Box”: from molecular to supramolecular pH-responsiveness

We present herein the development of a new polycationic cyclophane: the “red box”, second in a series of hydrazone-based analogues of the well-known organic receptor cyclobis(paraquat-p-phenylene)cyclophane (“blue box”).

Efficient and selective separation of aqueous sulfate through recognition and precipitation

Sulfate anions are selectively separated from aqueous solution in the form of precipitates by a mono-protonated organic receptor, constructed in situ through anion-templated chemical synthesis.

Insights into the electrooptical anion sensing properties of a new organic receptor: solvent dependent chromogenic response and DFT studies

AcO− ion mediated color transition properties of an organic receptor in solvents of varying polarity highlighting the influence of dipole moment in stabilizing the excited state.