Two benzothiadiazole-based compounds as multifunctional fluorescent sensors for detection of organic amines and anions

Qiu, Cheng-Qiang; Li, Le‐Qian; Shen, Yao; Liu, Sui‐Jun; Xu, Hui; Zheng, Teng‐Fei

doi:10.1016/j.poly.2021.115100

Cited by 8 publications

(5 citation statements)

References 44 publications

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“…13 C¬NMR (125 MHz, CDCl 3 ): δ 123.8 (4,7-C-btd), 129.3 (5,6-C-btd), 141.4 (3-C-Tr), 150.4 (4a,7a-C-btd), 196.3 (5-C-Tr). NMR data ( Figures S14 and S15 ) are consistent with the literature data [ 32 ].…”

Section: Methodssupporting

confidence: 88%

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A Zn(II)-Based Sql Type 2D Coordination Polymer as a Highly Sensitive and Selective Turn-On Fluorescent Probe for Al3+

2021

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A luminescent coordination polymer with the overall formula {[Zn(tr2btd)(bpdc)]∙DMF}n (where tr2btd = 4,7-di(1H-1,2,4-triazol-1-yl)-2,1,3-benzothiadiazole; bpdc = 4,4′-biphenyldicarboxylate) was synthesized and characterized by single-crystal and powder X-ray diffraction, thermogravimetric, infrared spectroscopy, and elemental analyses. Luminescent properties of the obtained compound were studied in detail both in the solid state and as a suspension in N,N-dimethylacetamide (DMA). It was found that {[Zn(tr2btd)(bpdc)]∙DMF}n exhibits bright turquoise luminescence with excellent quantum efficiency and demonstrates turn-on fluorescence enhancement effect upon soaking in DMA Al3+ solution. Fluorescence titration experiments were carried out and the detection limit for Al3+ ions was calculated to be 120 nM, which is among the lowest reported values for similar materials. Moreover, compound demonstrated excellent selectivity and reusability, and the mechanism of the response is discussed. These results indicate that {[Zn(tr2btd)(bpdc)]∙DMF}n is a promising probe for sensitive fluorescent Al3+ detection.

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Section: Methodssupporting

confidence: 88%

“…The tr 2 btd ligand was synthesized in a moderate yield by the reaction of Br 2 btd with 1H-1,2,4-triazole in a superbasic medium K 3 PO 4 –DMSO ( Scheme 1 ), the pure product was obtained by simple recrystallization, which presents an advantage compared to the previously reported method that requires column chromatography [ 32 ].…”

Section: Resultsmentioning

confidence: 99%

A Zn(II)-Based Sql Type 2D Coordination Polymer as a Highly Sensitive and Selective Turn-On Fluorescent Probe for Al3+

2021

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“…Based on the work of Liu and coworkers, 4,7-dibromo [2,1,3]benzothiazole (BTD-Br 2 ) was reacted with pyrazole under Cu-catalyzed coupling conditions, using CuI as the catalyst and 1,10-phenanthroline (phen) as the ligand, in the presence of K 2 CO 3 as base and DMF as the solvent. 38,39 Under these conditions, the desired product was isolated in 33% yield (Table 1, entry 1), which, albeit only moderately, is in accordance with the results obtained by the authors. In an attempt to improve the reaction yield, the base was changed to NaOtBu, but the efficiency of the reaction was the same (entry 2).…”

Section: Synthesis Of Btd-n-heterocycle Derivativessupporting

confidence: 90%

“…In 2019, Liu and coworkers reported a pyrazole-BTD conjugate that was used for the detection of Cu( ii ) and hydroxide by fluorescence spectroscopy. 38,39 Recently, Scholten and coworkers reported that ionic BTD-imidazole derivatives were efficient biosensors for cholesterol detection 40 while Neto and coworkers described pyridine-BTD derivatives that were applied as plasma membrane fluorescent markers. 41 On the other hand, different BTD-amine derivatives have been developed for uses as semiconductors for solar cells, 42 red-fluorescent emitters, 43 and charge-transport emitters for OLED technology.…”

Section: Introductionmentioning

confidence: 99%

Photoactive benzothiadiazole-N-heterocycle derivatives: synthesis, photophysics and water sensing in organic solvents

Ebersol,

Debia,

Zimba

et al. 2024

New J. Chem.

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“…Different heterocycles have been proposed in the literature as signaling units, generally conjugated and planar compounds capable of displaying color and fluorescence. Some examples include imidazoles [132][133][134][135], phenazines [136,137], rhodamines [138][139][140], and coumarins [141][142][143][144], among others [145][146][147][148][149][150][151][152][153][154][155][156][157][158][159][160][161][162].…”

Section: Strategies For Building Mlgs Based On Molecular Architecturementioning

confidence: 99%

Input Selection Drives Molecular Logic Gate Design

Souto,

Dias

2023

Analytica

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Optical detection devices have become an analytical tool of interest in diverse fields of science. The search for methods to identify and quantify different compounds has transposed this curiosity into a necessity, since some constituents threaten the safety of life in all its forms. In this context, 30 years ago, Prof. Prasanna de Silva presented the idea of sensors as Molecular Logic Gates (MLGs): a molecule that performs a logical operation based on one or more inputs (analytes) resulting in an output (optical modification such as fluorescence or absorption). In this review, we explore the implementation of MLGs based on the interference of a second input (second analyte) in suppressing or even blocking a first input (first analyte), often resulting in INHIBIT-type gates. This approach is interesting because it is not related to attached detecting groups in the MLG but to the relation between the first and the second input. In this sense, flexible and versatile MLGs can be straightforwardly designed based on input selection. To illustrate these cases, we selected examples seeking to diversify the inputs (first analytes and interfering analytes), outputs (turn on, turn off), optical response (fluorescent/colorimetric), and applicability of these MLGs.

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Two benzothiadiazole-based compounds as multifunctional fluorescent sensors for detection of organic amines and anions

Cited by 8 publications

References 44 publications

A Zn(II)-Based Sql Type 2D Coordination Polymer as a Highly Sensitive and Selective Turn-On Fluorescent Probe for Al3+

A Zn(II)-Based Sql Type 2D Coordination Polymer as a Highly Sensitive and Selective Turn-On Fluorescent Probe for Al3+

Photoactive benzothiadiazole-N-heterocycle derivatives: synthesis, photophysics and water sensing in organic solvents

Input Selection Drives Molecular Logic Gate Design

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