Design of a Pyrene Scaffold Multifunctional Material: Real-Time Turn-On Chemosensor for Nitric Oxide, AIEE Behavior, and Detection of TNP Explosive

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2019 Aug 29

PMID 31459160

Citations 4

Authors

Abu Saleh Musha Islam

Mihir Sasmal

Debjani Maiti

Ananya Dutta

Bibhutibhushan Show

Mahammad Ali

Affiliations

Soon will be listed here.

Abstract

A dual-emission pyrene-based new fluorescent probe (-(4-nitro-phenyl)-'-pyren-1-ylmethyl-ene-ethane-1,2-diamine (PyDA-NP)) displays green fluorescence for nitric oxide (NO) sensing, whereas it exhibits blue emission in the aggregated state. The mechanism of nitric oxide (NO/NO) sensing is based on N-nitrosation of aromatic secondary amine, which was not interfered by reactive oxygen species and reactive nitrogen species. The aggregation-induced enhancement of emission (AIEE) behaviors of the PyDA-NP could be attributed to the restriction of intramolecular rotation and vibration, resulting in rigidity enhancement of the molecules. The AIEE behavior of the probe was well established from fluorescence, dynamic light scattering, scanning electron microscopy, transmission electron microscopy, X-ray diffraction, optical fluorescence microscopy, and time-resolved photoluminescence studies. In a HO/CHCN binary mixture (8:2 v/v), the probe showed maximum aggregation with extensive (833-fold) increases in fluorescence intensity and high quantum yield (0.79). The aggregated state of the probe was further applied for the detection of nitroexplosives. It displayed efficient sensing of 2,4,6-trinitrophenol (TNP), corroborating mainly the charge-transfer process from pyrene to a highly electron-deficient TNP moiety. Furthermore, for the on-site practical application of the proposed analytical system, a contact-mode analysis was performed.

Citing Articles

Aggregation-Induced Emission Luminogen: Role in Biopsy for Precision Medicine.

Duo Y, Han L, Yang Y, Wang Z, Wang L, Chen J Chem Rev. 2024; 124(20):11242-11347.

PMID: 39380213 PMC: 11503637. DOI: 10.1021/acs.chemrev.4c00244.

Discriminative 'Turn-on' Detection of Al and Ga Ions as Well as Aspartic Acid by Two Fluorescent Chemosensors.

Goyal H, Annan I, Ahluwalia D, Bag A, Gupta R Sensors (Basel). 2023; 23(4).

PMID: 36850396 PMC: 9964346. DOI: 10.3390/s23041798.

Interpol review of detection and characterization of explosives and explosives residues 2016-2019.

Klapec D, Czarnopys G, Pannuto J Forensic Sci Int Synerg. 2021; 2:670-700.

PMID: 33385149 PMC: 7770463. DOI: 10.1016/j.fsisyn.2020.01.020.

Aggregation-Induced Emission-Active Hydrazide-Based Probe: Selective Sensing of Al, HF , and Nitro Explosives.

Dey S, Purkait R, Pal K, Jana K, Sinha C ACS Omega. 2019; 4(5):8451-8464.

PMID: 31459934 PMC: 6648475. DOI: 10.1021/acsomega.9b00369.

References

McQuade D, Pullen A, Swager T . Conjugated polymer-based chemical sensors. Chem Rev. 2001; 100(7):2537-74. DOI: 10.1021/cr9801014. View

Wurthner F, Kaiser T, Saha-Moller C . J-aggregates: from serendipitous discovery to supramolecular engineering of functional dye materials. Angew Chem Int Ed Engl. 2011; 50(15):3376-410. DOI: 10.1002/anie.201002307. View

Islam A, Bhowmick R, Pal K, Katarkar A, Chaudhuri K, Ali M . A Smart Molecule for Selective Sensing of Nitric Oxide: Conversion of NO to HSNO; Relevance of Biological HSNO Formation. Inorg Chem. 2017; 56(8):4324-4331. DOI: 10.1021/acs.inorgchem.6b02787. View

Broniowska K, Diers A, Hogg N . S-nitrosoglutathione. Biochim Biophys Acta. 2013; 1830(5):3173-81. PMC: 3679660. DOI: 10.1016/j.bbagen.2013.02.004. View

Furchgott R . Endothelium-Derived Relaxing Factor: Discovery, Early Studies, and Identifcation as Nitric Oxide (Nobel Lecture). Angew Chem Int Ed Engl. 2021; 38(13-14):1870-1880. DOI: 10.1002/(SICI)1521-3773(19990712)38:13/14<1870::AID-ANIE1870>3.0.CO;2-8. View

Salinas Y, Martinez-Manez R, Marcos M, Sancenon F, Costero A, Parra M . Optical chemosensors and reagents to detect explosives. Chem Soc Rev. 2011; 41(3):1261-96. DOI: 10.1039/c1cs15173h. View

Mei J, Hong Y, Lam J, Qin A, Tang Y, Tang B . Aggregation-induced emission: the whole is more brilliant than the parts. Adv Mater. 2014; 26(31):5429-79. DOI: 10.1002/adma.201401356. View

Beltran A, Isabel Burguete M, Abanades D, Perez-Sala D, Luis S, Galindo F . Turn-on fluorescent probes for nitric oxide sensing based on the ortho-hydroxyamino structure showing no interference with dehydroascorbic acid. Chem Commun (Camb). 2014; 50(27):3579-81. DOI: 10.1039/c3cc49555h. View

Kaiser T, Wang H, Stepanenko V, Wurthner F . Supramolecular construction of fluorescent J-aggregates based on hydrogen-bonded perylene dyes. Angew Chem Int Ed Engl. 2007; 46(29):5541-4. DOI: 10.1002/anie.200701139. View

10.

Zhang Z, Chen S, Shi R, Ji J, Wang D, Jin S . A single molecular fluorescent probe for selective and sensitive detection of nitroaromatic explosives: A new strategy for the mask-free discrimination of TNT and TNP within same sample. Talanta. 2017; 166:228-233. DOI: 10.1016/j.talanta.2017.01.046. View

11.

Miao J, Huo Y, Lv X, Li Z, Cao H, Shi H . Fast-response and highly selective fluorescent probes for biological signaling molecule NO based on N-nitrosation of electron-rich aromatic secondary amines. Biomaterials. 2015; 78:11-9. DOI: 10.1016/j.biomaterials.2015.11.011. View

12.

Dey N, Samanta S, Bhattacharya S . Selective and efficient detection of nitro-aromatic explosives in multiple media including water, micelles, organogel, and solid support. ACS Appl Mater Interfaces. 2013; 5(17):8394-400. DOI: 10.1021/am401608q. View

13.

Ye X, Rubakhin S, Sweedler J . Simultaneous nitric oxide and dehydroascorbic acid imaging by combining diaminofluoresceins and diaminorhodamines. J Neurosci Methods. 2007; 168(2):373-82. PMC: 2291520. DOI: 10.1016/j.jneumeth.2007.10.026. View

14.

Yu H, Xiao Y, Jin L . A lysosome-targetable and two-photon fluorescent probe for monitoring endogenous and exogenous nitric oxide in living cells. J Am Chem Soc. 2012; 134(42):17486-9. DOI: 10.1021/ja308967u. View

15.

Yang Y, Seidlits S, Adams M, Lynch V, Schmidt C, Anslyn E . A highly selective low-background fluorescent imaging agent for nitric oxide. J Am Chem Soc. 2010; 132(38):13114-6. DOI: 10.1021/ja1040013. View

16.

Lv X, Wang Y, Zhang S, Liu Y, Zhang J, Guo W . A specific fluorescent probe for NO based on a new NO-binding group. Chem Commun (Camb). 2014; 50(56):7499-502. DOI: 10.1039/c4cc03540b. View

17.

Kartha K, Sandeep A, Praveen V, Ajayaghosh A . Detection of nitroaromatic explosives with fluorescent molecular assemblies and π-gels. Chem Rec. 2014; 15(1):252-65. DOI: 10.1002/tcr.201402063. View

18.

Nagarkar S, Desai A, Samanta P, Ghosh S . Aqueous phase selective detection of 2,4,6-trinitrophenol using a fluorescent metal-organic framework with a pendant recognition site. Dalton Trans. 2015; 44(34):15175-80. DOI: 10.1039/c5dt00397k. View

19.

Desai A, Samanta P, Manna B, Ghosh S . Aqueous phase nitric oxide detection by an amine-decorated metal-organic framework. Chem Commun (Camb). 2015; 51(28):6111-4. DOI: 10.1039/c5cc00773a. View

20.

Kartha K, Babu S, Srinivasan S, Ajayaghosh A . Attogram sensing of trinitrotoluene with a self-assembled molecular gelator. J Am Chem Soc. 2012; 134(10):4834-41. DOI: 10.1021/ja210728c. View