Chemical Sensing Technology towards Global Public Safety (I): Fluorescent Probes for Detection of Phosgene

doi:10.21127/yaoyigc20220011

Abstract

Abstract: Phosgene, an important chemical warfare agent (CWA), has received great attention in the field of counterterrorism and public safety monitoring. Developing new sensing methods/tools for efficient detection of phosgene is an urgent challenge to be solved. For chemists, it is pivotal to create fast, low cost, portable, selective, sensitive, as well as visualizable chemical sensors/probes for real-time phosgene detection. This article reviewed and discussed current trend and statement of phosgene-specific fluorescent probes, providing concise “fast glance” and systematic “big picture” to the related researchers and public safety engineers. Moreover, the outlook in this field was also stated.

Key words: fluorescent probes, chemical warfare agents, phosgene, perspective

Ruilong Sheng. Chemical Sensing Technology towards Global Public Safety (I): Fluorescent Probes for Detection of Phosgene[J]. General Chemistry, 2023, 9(3-4): 220011-220011.

References

[1] (a) Plahovinsak, J.; Perry, M.; Knostman, K.; Segal, R.; Babin, M. Characterization of a nose-only inhaled phosgene acute lung injury mouse model. Inhal. Toxicol. 2015, 27, 832–840;
(b) Li, W.; Rosenbruch, M.; Pauluhn, J. Effect of PEEP on phosgene-induced lung edema: pilot study on dogs using protective ventilation strategies. Exp. Toxical. Pathol. 2015, 67, 109–116;
(c) Holmes, W.; Keyser, B.; Paradiso, D.; Ray, R.; Andres, D.; Benton, B.; Rothwell, C.; Hoard-Fruchey, H.; Dillman, J.; Sciuto, A.; Anderson, D. Conceptual approaches for treatment of phosgene i nhalation-induced lung injury. Toxicol. Lett. 2016, 244, 8–20.
[2] (a) Chen, L.; Wu, D.; Yoon, J. Recent advances in the development of chromophore-based chemosensors for nerve agents and phosgene. ACS Sens. 2018, 3, 27–43;
(b) Wu, D.; Sedgwick, A.; Gunnlaugsson, T.; Akkaya, E.; Yoon, J.; James, T. Fluorescent chemosensors: the past, present and future. Chem. Soc. Rev. 2017, 46, 7105–7123;
(c) Tan, J.; Li, Z.; Lu, Z.; Chang, R.; Sun, Z.; You, J. Recent progress in the development of chemodosimeters for fluorescence visualization of phosgene. Dyes Pigments 2021, 193, 109540;
(d) Zhu, B.; Sheng, R.; Chen, T.; Rodrigues, J.; Song, Q.; Hu, X.; Zeng, L. Molecular engineered optical probes for chemical warfare agents and their mimics: Advances, challenges and perspectives. Coord. Chem. Rev. 2022, 463, 214527.
[3] (a) Xia, H.; Xu, X.; Song, Q. BODIPY-based fluorescent sensor for the recognization of phosgene in solutions and in gas phase. Anal. Chem. 2017, 89, 4192–4197;
(b) Sayar, M.; Karakus, E.; Güener, T.; Yildiz, B.; Yildiz, U.; Emrullahoğlu, M. A BODIPY-based fluorescent probe to visually detect phosgene: toward the development of a handheld phosgene detector. Chem. Eur. J. 2018, 24, 3136–3140;
(c) Hu, Y.; Chen, L.; Jung, H.; Zeng, Y.; Lee, S.; Swamy, K.; Zhou, X.; Kim, M. H.; Yoon, J. Effective strategy for colorimetric and fluorescence sensing of phosgene based on small organic dyes and nanofiber platforms. ACS Appl. Mater. Interfaces 2016, 8, 22246–22252;
(d) Xia, H.; Xu, X.; Song, Q. Fluorescent chemosensor for selective detection of phosgene in solutions and in gas phase. ACS Sens. 2017, 2, 178–182;
(e) Zhang, Y.; Peng, A.; Jie, X.; Lv, Y.; Wang, X.; Tian, Z. A BODIPY-based fluorescent probe for detection of subnanomolar phosgene with rapid response and high selectivity. ACS Appl. Mater. Interfaces 2017, 9, 13920–13927;
(f) Zhou, X.; Zeng, Y.; Liyan, C.; Wu, X.; Yoon, J. A Fluorescent Sensor for Dual-Channel Discrimination between Phosgene and a Nerve-Gas Mimic. Angew. Chem. Int. Ed. 2016, 55, 4729–4733;
(g) Kim, T.; Kim, D.; Bouffard, J.; Kim, Y. Rapid, specific, and ultrasensitive fluorogenic sensing of phosgene through an enhanced PeT mechanism. Sens. Actuators B 2019, 283, 458–462.
[4] Zhang, W.; Cheng, K.; Yang, X.; Li, Q.; Zhang, H.; Ma, Z.; Lu, H.; Wu, H.; Wang, X. A benzothiadiazole-based fluorescent sensor for selective detection of oxalyl chloride and phosgene. Org. Chem. Front. 2017, 4, 1719–1725.
[5] Kim, T.; Hwang, B.; Bouffard, J.; Kim. Y. Instantaneous Colorimetric and Fluorogenic Detection of Phosgene with a me-so-Oxime-BODIPY. Anal. Chem. 2017, 89, 12837–12842.
[6] Kundu, P.; Hwang, K. Rational design of fluorescent phosgene sensors. Anal. Chem. 2012, 84, 4594–4597.
[7] (a) Wu, X.; Wu, Z.; Yang, Y.; Ha, S. A highly sensitive fluorogenic chemodosimeter for rapid visual detection of phosgene. Chem. Commun. 2012, 48, 1895–1897.;
(b) Hu, Y.; Zhou, X.; Jung, H.; Nam, S.; Kim, M.; Yoon, J. Colorimetric and fluorescent detecting phosgene by a second-generation chemosensor. Anal. Chem. 2018, 90, 3382–3386.
[8] Xie, H.; Wu, Y.; Zeng, F.; Chen, J.; Wu, S. An AIE-based fluorescent test strip for the portable detection of gaseous phosgene. Chem. Commun. 2017, 53, 9813–9816.
[9] Wang, S.; Zhong, L.; Song, Q. A ratiometric fluorescent chemosensor for selective and visual detection of phosgene in solutions and in the gas phase. Chem. Commun. 2017, 53, 1530–1533.
[10] Chen, L.; Wu, D.; Kim, J.; Yoon, J. An ESIPT-based fluorescence probe for colorimetric, ratiometric, and selective detection of phosgene in solutions and the gas phase. Anal. Chem. 2017, 89, 12596–12601.
[11] Hu, Q.; Duan, C.; Wu, J.; Su, D.; Zeng, L.; Sheng, R. Colorimetric and ratiometric chemosensor for visual detection of gaseous phosgene based on anthracene carboxyimide membrane. Anal. Chem. 2018, 90, 8686–8691.
[12] (a) Wu, J.; Su, D.; Li, W.; Xia, C.; Rodrigues, J.; Sheng, R.; Zeng, L. A fast responsive chromogenic and near-infrared fluorescence lighting-up probe for visual detection of toxic thiophenol in environmental water and living cells. Talanta 2019, 201, 111–118.;
(b) Ye, Z.; Duan, C.; Sheng, R.; Xu, J.; Wang, H.; Zeng, L. A novel colorimetric and ratiometric fluorescent probe for visualizing SO2 derivatives in environment and living cells. Talanta 2018, 176, 389–396;
(c) Sheng, R.; Ma, J.; Wang, P.; Liu, W.; Wu, J.; Li, H.; Zhuang, X.; Zhang, H.; Wu, S. Enzyme sensing based on a controllable oxidation reaction. Biosens. Bioelectron. 2010, 26, 949–952;
(d) Xu, J.; Niu, G.; Wei, X.; Lan, M.; Zeng, L.; Kinsella, J.; Sheng, R. A family of multi-color anthracene carboxyimides: Synthesis, spectroscopic properties, solvatochromic fluorescence and bio-imaging application. Dyes Pigments 2017, 139, 166–173.
[13] Adaikalam Shylaja, A.; Roja, S.; Priya, R.; Kumar, R. Four- Component Domino Synthesis of Pyrazolo[3,4-h] quinoline-3- carbonitriles: “Turn-Off” Fluorescent Chemosensor for Fe3+ Ions. J. Org. Chem. 2018, 83, 14084–14090.
[14] Yan, J.; Lee, S.; Zhang, A.; Yoon, J. Self-immolative colorimetric, fluorescent and chemiluminescent chemosensors. Chem. Soc. Rev. 2018, 47, 6900–6916.
[15] Ye, H.; Ke, Y.; Yue, C.; Xie, P.; Sheng, R.; Zeng, L. 5G smartphone- adaptable fluorescence sensing platform for simultaneous detection of toxic formaldehyde and phosgene in different emission channels. Dyes Pigments 2022, 207, 110782.
[16] Long, Y.; Qian, R. Wearable chemosensors: A review of recent progress. ChemistryOpen 2018, 7, 118–130.