A novel, selective, and extremely responsive thienyl-based dual fluorogenic probe for tandem superoxide and Hg<sup>2+</sup>chemosensing

Singh, Atul Pratap; Murale, Dhiraj P.; Ha, Yonghwang; Liew, Hyunjeong; Lee, Kang Mun; Segev, Aviv; Suh, Yoo‐Hun; Churchill, David G.

doi:10.1039/c2dt32135a

Cited by 38 publications

(17 citation statements)

References 57 publications

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“…Hg 2+ coordinates to pyridyl sulfide and thienyl bearing receptors, improving the rigidity and thus the fluorescence quantum yield of the probe. 26 Oxidation of sulfide by superoxide further enhances the fluorescence. Even though the probe cannot be investigated in a neuroblastoma cell line in the presence of both inputs due to the chelation of Hg 2+ by cellular thiols, in vitro analysis demonstrates a dual AND logic response of the sensor.…”

Section: Chemical Logic Gates In Biological Mediamentioning

confidence: 99%

Molecular logic gates: the past, present and future

et al. 2018

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The field of molecular logic gates originated 25 years ago, when A. P. de Silva published a seminal article in Nature. Stimulated by this ground breaking research, scientists were inspired to join the race to simulate the workings of the fundamental components of integrated circuits using molecules. The rules of this game of mimicry were flexible, and have evolved and morphed over the years. This tutorial review takes a look back on and provides an overview of the birth and growth of the field of molecular logics. Spinning-off from chemosensor research, molecular logic gates quickly proved themselves to be more than intellectual exercises and are now poised for many potential practical applications. The ultimate goal of this vein of research became clearer only recently - to "boldly go where no silicon-based logic gate has gone before" and seek out a new deeper understanding of life inside tissues and cells.

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Section: Chemical Logic Gates In Biological Mediamentioning

confidence: 99%

Molecular logic gates: the past, present and future

et al. 2018

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“…The group of Churchill pioneered the synthesis of meso ‐thienyl‐substituted corroles and their building blocks, and studied their characteristics . Through these investigations, it became clear that the presence of the meso ‐thienyl‐substituents in corroles (and dipyrrin‐based chromophores, such as boron‐dipyrromethene (BODIPY)) have a significant effect on the electronic structure and photophysical properties of the chromophores. However, we are not aware of a detailed description of the nature of the electronic interactions between the thienyl moieties and the central corrole chromophore.…”

Section: Introductionmentioning

confidence: 99%

A Spectroscopic and Theoretical Investigation of a Free‐Base meso‐Trithienylcorrole

Greco

Rossi

Birge

et al. 2013

Photochem & Photobiology

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The unique optical properties of free-base meso-trithienylcorrole were compared to those of the widely investigated meso-triphenyl-substituted analogue. A combination of spectroscopic and computational experiments were undertaken to elucidate the relationship between structural features of the neutral, mono-anionic, and mono-cationic forms of the corroles and their corresponding optical properties. A general bathochromic shift was measured for the thienyl-substituted corrole. The experimental spectra are supported by excited state calculations. A systematic series of ground state minimizations were performed to determine energy minima for the flexible and solvent-sensitive molecules. Trithienylcorrole was found to have a more non-planar macrocycle in conjunction with a high degree of π-overlap with the meso-substituents. Both structural features contribute to their bathochromically shifted optical spectra. The configurational character of the thienyl-substituted corrole is shown to have a larger degree of molecular orbital mixing and doubly excited character, which suggest a more complex electronic structure that does not fully adhere to the Gouterman four-orbital model. The reactivity of the thienyl groups, particularly with respect to their ability to be (electro)-polymerized, combined with the tight coupling of the meso-thienyl groups with the corrole chromophore elucidated in this work, recommends the meso-thienylcorroles as building blocks in, for instance, organic semiconductor devices.

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“…28 The binding receptor [S thi ,N py ] or [S thi ,N py ,N py ] of such PeT-based probes acts as a quencher due to its high electron-donating ability, until the coordination of the Hg(II) cation. In addition to suppressing the PeT process, metal chelation leads to enhanced steric rigidity of the mesoaryl group which may further help fluorescence recovery.…”

Section: Metal Complexation and Oxidation Reactionmentioning

confidence: 99%

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confidence: 99%

“AND” luminescent “reactive” molecular logic gates: a gateway to multi-analyte bioimaging and biosensing

Romieu

2015

Org. Biomol. Chem.

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This review outlines examples that illustrate a recent and highly innovative concept in the field of (bio)molecular sensing, namely the simultaneous multi-analyte detection using "reactive" luminescent probes that are able to produce an optical signal only in response to multiple (bio)chemical inputs and through covalent chemical reactions with target (bio)analytes. Unlike conventional "AND" molecular logic gates based on supramolecular photochemical mechanisms, these unusual "smart" optical (bio)probes are suitable tools to track the rise and fall of a wider range of biologically relevant analytes, in complex media and with higher selectivity. The potential utility of this concept for in vivo molecular imaging and possible solutions to adapt the described luminogenic processes to far-red or NIR emitters are also discussed.

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A novel, selective, and extremely responsive thienyl-based dual fluorogenic probe for tandem superoxide and Hg²⁺chemosensing

Cited by 38 publications

References 57 publications

Molecular logic gates: the past, present and future

Molecular logic gates: the past, present and future

A Spectroscopic and Theoretical Investigation of a Free‐Base meso‐Trithienylcorrole

“AND” luminescent “reactive” molecular logic gates: a gateway to multi-analyte bioimaging and biosensing

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A novel, selective, and extremely responsive thienyl-based dual fluorogenic probe for tandem superoxide and Hg2+chemosensing

Cited by 38 publications

References 57 publications

Molecular logic gates: the past, present and future

Molecular logic gates: the past, present and future

A Spectroscopic and Theoretical Investigation of a Free‐Base meso‐Trithienylcorrole

“AND” luminescent “reactive” molecular logic gates: a gateway to multi-analyte bioimaging and biosensing

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A novel, selective, and extremely responsive thienyl-based dual fluorogenic probe for tandem superoxide and Hg²⁺chemosensing