Metal ion detection by luminescent 1,3-bis(dimethylaminomethyl) phenyl receptor-modified chromophores and cruciforms

Mangalum, Anshuman; Gilliard, Robert J.; Hanley, Jessica M.; Parker, A.; Smith, Rhett C.

doi:10.1039/c0ob00156b

Cited by 20 publications

(16 citation statements)

References 29 publications

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“…ESI-TOF-MS spectra were recorded on Agilent 6210 TOF spectrometer. 4-(Hexyloxy)benzaldehyde 2 [30], 1-(hexyloxy)-4-vinylbenzene 4 [28], 7-bromo-9,9-dihexyl-9H-fluorene-2-carbaldehyde 6 [29] were prepared according to literature procedures.…”

Section: Methodsmentioning

confidence: 99%

Computer aided chemical design: using quantum chemical calculations to predict properties of a series of halochromic guaiazulene derivatives

et al. 2016

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With the scientific community becoming increasingly aware of the need for greener products and methodologies, the optimization of synthetic design is of greater importance. Building on experimental data collected from a synthesized guaiazulene derivative, a series of analogous structures were investigated with time-dependent density functional theory (TD-DFT) methods in an effort to identify a compound with desirable photophysical properties. This in silico analysis may eliminate the need to synthesize numerous materials that, when investigated, do not possess viable characteristics. The synthesis of several computationally investigated structures revealed discrepancies in the calculation results. Further refined computational study of the molecules yielded results closer to those observed experimentally and helps set the stage for computationally guided design of organic photonic materials. Three novel derivatives were synthesized from guaiazulene, a naturally occurring chromophore, exhibiting distinct halochromic behaviour, which may have potential in a switchable optoelectronic system or combined with a photoacid generator for data storage. The protonated forms were readily excitable via two-photon absorption.

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Section: Methodsmentioning

confidence: 99%

Computer aided chemical design: using quantum chemical calculations to predict properties of a series of halochromic guaiazulene derivatives

et al. 2016

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“…The latter was then coupled with trimethylsilylacetylene (TMSA) under Sonogashira-type cross-coupling conditions to yield bromoaryl 29, which was subsequently subjected to a second cross-coupling reaction with 2-ethynylaryl 30 (prepared according to reported procedures; [59][60][61] see the Supporting Information) to yield, after deprotection of the TMS protecting group, bisphenylethynyl derivative 32 in 63 % over three steps. Molecule 32 was then coupled with another equivalent of 1-bromo-4-iodoaryl derivative 28 to give bromo-terminating OPE derivative 33.…”

Section: Synthesis Of the Chromophoric Dyad Triads And Tetradsmentioning

confidence: 99%

Versatile Bisethynyl[60]fulleropyrrolidine Scaffolds for Mimicking Artificial Light‐Harvesting Photoreaction Centers

Kremer

Bietlot

Zanelli

et al. 2014

Chemistry A European J

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Fullerene-based tetrads, triads, and dyads are presented in which [60]fulleropyrrolidine synthons are linked to an oligo(p-phenyleneethynylene) antenna at the nitrogen atom and to electron-donor phenothiazine (PTZ) and/or ferrocene (Fc) moieties at the α carbon of the pyrrolidine cycle through an acetylene spacer. Cyclic voltammetry and UV/ Vis absorption spectra evidence negligible ground-state electronic interactions among the subunits. By contrast, strong excited-state interactions are detected upon selective light irradiation of the antenna (UV) or of the fullerene scaffold (Vis). When only PTZ is present as electron donor, photoinduced electron transfer to the fullerene unit is unambiguously detected in benzonitrile, but this is not the case when Fc is part of the multicomponent system. These results suggest that Fc is a formidable energy transfer quencher and caution should be used in choosing it as electron donor to promote efficient charge separation in multicomponent arrays.

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“…[44–46] Variants with non-conjugated amine substituents selectively interacted with Zn cations over other metals, while those with conjugated coordinating groups had differing responses. [47] These structurally simple systems provide superior HOMO–LUMO separation along the X and Y axes, yielding distinctive solvatochromic and analyte-sensitive spectroscopic changes.…”

Section: Charged Speciesmentioning

confidence: 99%

Ion and Molecular Recognition Using Aryl–Ethynyl Scaffolding

Vonnegut

Tresca

Johnson

et al. 2015

Chemistry An Asian Journal

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The aryl–ethynyl linkage has been extensively employed in the construction of hosts for a variety of guests. Uses range from ion detection (e.g., of metal cations in the environment or industrial waste and of anions prevalent in nature), to molecular mimics for biological systems, and to applications targeting future safety issues (such as CO2 capture and indicators for the manufacture of chemical weapons). This Focus Review examines the utilization of the aryl–ethynyl linkage in engineering host molecules for a variety of different guests, and how the alkyne unit plays an integral part as both a rigid scaffolding section in host geometry design as well as a linker to allow conjugative communication between discrete π-electron systems.

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Metal ion detection by luminescent 1,3-bis(dimethylaminomethyl) phenyl receptor-modified chromophores and cruciforms

Cited by 20 publications

References 29 publications

Computer aided chemical design: using quantum chemical calculations to predict properties of a series of halochromic guaiazulene derivatives

Computer aided chemical design: using quantum chemical calculations to predict properties of a series of halochromic guaiazulene derivatives

Versatile Bisethynyl[60]fulleropyrrolidine Scaffolds for Mimicking Artificial Light‐Harvesting Photoreaction Centers

Ion and Molecular Recognition Using Aryl–Ethynyl Scaffolding

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