Solid-state sensory properties of CALIX-poly(phenylene ethynylene)s toward nitroaromatic explosives

Costa, Alexandra I.; Pinto, Hugo D.; Ferreira, L. F. Vieira; Prata, José V.

doi:10.1016/j.snb.2011.11.017

Cited by 42 publications

(22 citation statements)

References 49 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…33,34 Since the containing of triphenylene motif in the TP-CMP promises its potential as luminescent material, the ability of TP-CMP to act as a nitrobenzene sensor was studied in the solid state according to similar procedures reported in literature. [28][29][30][31] As expected, the as synthesized CP-CMP shows a emission band centered at 500 nm with high intensity. When exposed to a saturated nitrobenzene atmosphere, it is observed that the emission intensity of TP-CMP is quenched about 18% within 1 min and about 85% within 30 min at room temperature ( Fig.…”

supporting

confidence: 80%

A triphenylene-based conjugated microporous polymer: construction, gas adsorption, and fluorescence detection properties

et al. 2015

View full text Add to dashboard Cite

A triphenylene-based conjugated microporous polymer (TP-CMP) has been synthesized and shows high surface area (S BET ¼ 1104 m 2 g À1 ) and remarkable uptakes of H 2 (7.08 mmol g À1 at 77 K and 900 mmHg) and CO 2 (3.37 mmol g À1 at 273 K and 900 mmHg). In addition, it could be utilized to detect nitrobenzene selectively via fluorescence quenching.Conjugated microporous polymers (CMPs) have many intrinsic advantages such as large specic surface area, high stability, easy functionalization and low skeleton density, which makes them good candidates as potential functional materials in the elds of gas storage and separations, 1-5 and heterogeneous catalysis. 6 In general, the building units play a crucial role in designing and controlling the structures and properties of CMPs. To date, a number of building units, for example 1,3,5-tribromobenzene, 7,8 1,2,4,5-tetrabromobenzene, 8 1,3,5-tris(4-bromophenyl)benzene, 9 hexa(4-bromophenyl)benzene, 10 1,3,5-tri(9-carbazolyl)benzene, 11 chloroiodosilole, 12 sprio-bis(2,5-dibromopropylenedioxythiophene), 13 tris(4-bromophenyl)-amine, 14 tetrakis(4-bromophenyl)methane, 15 tetrakis(4-cyanophenyl)methane, 16,17 2,6,14-tribromo-tritycene, 18 and triphenylene unit [19][20][21][22] have been utilized to construct various CMPs for the purpose of exploring basic structure-property relationships as well as practical applications.Among the various organic units with different structure and properties, triphenylene has been widely used in the preparation of luminescent and semiconducting optoelectronic device based on its rich optical and electronic properties. 21,[23][24][25] However, triphenylene is less reported in the research of CMPs compared to the other synthons. Considering about its rigid planar structure with large p system, CMPs composed with this motif could be expected to show high surface area and luminescent property, which is desired for gas sorption and uo-rescent detecting applications. Aiming at the exploration of functional CMPs, we focused on the construction and properties investigation of triphenylene based CMPs. Herein, we report a new triphenylene-based CMPs, namely TP-CMP (Scheme 1). As expected, the TP-CMP has a large BET surface area up to 1104 m 2 g À1 and can effectively adsorb H 2 (7.08 mmol g À1 at 900 mmHg and 77 K) and CO 2 (3.37 mmol g À1 at 900 mmHg and 273 K), respectively. Furthermore, TP-CMP exhibits strong uorescence emission, which can be utilized to the selective detection of nitrobenzene in DMF solution.The synthetic route to TP-CMP is depicted in Scheme 1. The detailed procedures are described in the ESI. † To realize the porous structure of triphenylene-based CMPs, 2,3,6,7,10,11-hexabromotriphenylene and 1,4-phenylenebisboronic acid were selected as reactants and connected through a phenyl-phenyl coupling reaction. The formation of TP-CMP can be certied by the Fourier transform infrared (FTIR) spectroscopy and solid state 13 C/MAS NMR measurement. The absence of C-Br (511 cm À1 ) and C-B (1343 cm À1 ) stretching peak in the FTIR spectra ...

show abstract

supporting

confidence: 80%

A triphenylene-based conjugated microporous polymer: construction, gas adsorption, and fluorescence detection properties

et al. 2015

View full text Add to dashboard Cite

show abstract

“…11,12 Conjugated polymers are one of the hot research topics both in academic and industry, and calix [4]arenes were incorporated as a pendant side group, which enhanced the polymer solubility and was utilized as sensors toward various classes of molecules. [13][14][15][16][17][18][19] On the other hands, calixarenes are known to have a rigid structure, making their incorporation into a polymer backbone relatively difficult unless exible solubilizing groups are introduced at the same time. Dondoni et al synthesized a bisphenol A-type polymer having a calix [4]arene moiety in its main chain and studied Ag ion recognition.…”

Section: Introductionmentioning

confidence: 99%

Excellent performance of aromatic polyguanamines induced by multiple hydrogen bondable tetraazacalix[2]arene[2]-triazine ring in their main chain

et al. 2020

View full text Add to dashboard Cite

show abstract

“…The combined components in such systems are expected to act cooperatively in order to enhance the signalling events related to a particular hostguest interaction. Calix [4]arenes, a well-known class of synthetic molecular receptors, have been explored as supramolecular scaffolds in several luminescent-based chemosensing schemes, either attached as pendant groups to conjugated polymers (CPs) (4)(5)(6)(7)(8)(9) or as part of the main chain motif (10,11), as well as in single-molecule (SM) chemosensors (12,13). In addition, carbazole-derived lowmolar mass molecular materials and p-CPs have shown their utility as transduction elements in chemical sensors (14)(15)(16)(17)(18)(19)(20)(21).…”

Section: Introductionmentioning

confidence: 99%

New entities for sensory chemistry based on calix[4]arene-carbazole conjugates: from synthesis to applications

Barata

Prata

2013

Supramolecular Chemistry

Self Cite

View full text Add to dashboard Cite

Two new calix [4]arene-carbazole conjugates (CALIX-CBZs) comprising 2-and 3-ethynyl-substituted carbazole derivatives attached to a central bis-calix[4]arene-containing phenylene ring have been designed for fluorescence-based detection of high explosive materials and explosive markers in vapour phase. The title compounds were prepared in good isolated yields and structurally fully characterised. CALIX-CBZs are highly fluorescent compounds that largely preserve their deep blue luminescence in solid state with no notorious emissions from electronic aggregated states. The excellent optical properties exhibited by casted films of both materials, including their photochemical stability, suggested their potential use as solidstate sensors. Remarkable high and fast responses were in fact retrieved upon contact with saturated vapours of 2,4,6-trinitrotoluene (TNT, a high explosive) and 2,4-dinitrotoluene (a common impurity in TNT batches, often used as its chemical marker), reaching near 80% of fluorescence quenching for the later on 30 s of exposure. Experiments performed with nitroaliphatic compounds (nitromethane (NM), a liquid explosive and 2,3-dimethyl-2,3-dinitrobutane, an explosive taggant) also revealed a high level of sensitivity (up to near 40% fluorescence quenching in only 10 s of exposure to NM). The quenching efficiencies were overall correlated with the extent and strength of CALIX-CBZs -analyte interactions, the vapour pressure of the analytes and the film thicknesses.

show abstract

Solid-state sensory properties of CALIX-poly(phenylene ethynylene)s toward nitroaromatic explosives

Cited by 42 publications

References 49 publications

A triphenylene-based conjugated microporous polymer: construction, gas adsorption, and fluorescence detection properties

A triphenylene-based conjugated microporous polymer: construction, gas adsorption, and fluorescence detection properties

Excellent performance of aromatic polyguanamines induced by multiple hydrogen bondable tetraazacalix[2]arene[2]-triazine ring in their main chain

New entities for sensory chemistry based on calix[4]arene-carbazole conjugates: from synthesis to applications

Contact Info

Product

Resources

About