Self-Assembly Hydrosoluble Coronenes: A Rich Source of Supramolecular Turn-On Fluorogenic Sensing Materials in Aqueous Media

Abstract

Water-soluble coronenes, that form nanoparticles by self-association, work as new fluorescent materials by complexation with cucurbit[7]uril, as well as selective turn-on fluorogenic sensors for nitroaromatic explosives with remarkable selectivity, by using only water as solvent.

Synthesis of water-soluble hemicoronenediimides by photocyclization of perylenediimides: Turn-on fluorescent probes in water by complexation with Cucurbit[7]uril or binding to G-quadruplex Motifs

“…Our synthesis started by the Suzuki reaction of the bromoperylenediimide 1 with one equivalent of a N-Boc protected piperazinylpyrimidine boronic ester 2 (Scheme 1) in conditions previously established by the group for related Suzuki reactions [38][39][40] The N-Boc protected derivative 3 (90% yield) was obtained after work-up of the reaction. Irradiation of 3 in dichloromethane (DCM) under visible light (halogen lamp, 50W, 4 cm distance) and open air for 3 h, gave 4 (95% yield).…”

Silica Nanoparticle/Fluorescent Dye Assembly Capable of Ultrasensitively Detecting Airborne Triacetone Triperoxide: Proof-of-Concept Detection of Improvised Explosive Devices in the Workroom

“…TATP sublimes easily at room temperature, but, because of the lack of aromatic nitro groups, its presence in the vapor phase is not detected by using common methods for explosives . Common explosives containing nitro groups, such as trinitrotoluene (TNT), have a large variety of fluorescent methods for their detection, including our contribution to the field and from other groups. − Another explosive employed in IEDs which is also important, hexamethylene triperoxide diamine (HMTD), has a much lower vapor pressure than TATP. Unfortunately, the detection of HMTD in the vapor phase is not possible .…”

A Metal-Free Triazacoronene-Based Bimodal VOC Sensor

“…30,39−43 Developing materials with considerable π-orderings is viable for making high-performance optoelectronic devices and compelling interplay with holes, electrons, photons, and excitons. 30,31,44,45 Intrigued these studies, we synthesized a thiophenefunctionalized triazacoronene (TTAC, Scheme 1) based PAH and investigated highly hazardous VOC sensing performance by monitoring optical and electrical responses. The TTAC constitutes an electron-deficient nitrogen-substituted coronene π-disk at the center acting as an electron acceptor and thiophene blades at the periphery acting as an electron donor to form a donor−acceptor−donor (D−A−D) π-array.…”

“…The phenomena were attributed to the required coplanarity of the TAC core. − The π - ordering and optoelectronic property tuning can also be possible by systematic periphery extension and functionalization . The synergistic utilization of desired functional groups at the periphery and predesigned π - channels of the coronene core offers various possibilities for optoelectronic applications, such as organic light-emitting diodes, field effect transistors, photovoltaics, and sensors. ,− Developing materials with considerable π - orderings is viable for making high-performance optoelectronic devices and compelling interplay with holes, electrons, photons, and excitons. ,,, …”

“…The coronene or hexabenzocoronene (HBC) based polycyclic aromatic hydrocarbons (PAHs) have shown great potential in various optoelectronic applications because of their unique graphitic structure, ordered π-channel for hole/electron conductions, and manageable optical and electronic properties. − Notably, these opportunities rely on the possibility of custom functionalization of the PAH core, synthetic success, solution processability, and stability. − Several studies revealed that the heteroatom (N, O, S) doping into the nanographitic coronene-based PAHs significantly altered their physicochemical properties. For example, the ‘N’ doped PAH, 1,5,9-triazacoronene (TAC), is an electron-deficient core suitable for electron conduction (n-type semiconductor) .…”