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Synlett 2022; 33(14): 1335-1340
DOI: 10.1055/a-1806-6258
DOI: 10.1055/a-1806-6258
cluster
Organic Chemistry in Thailand
2,3-Diaryl-1,1,4,4-tetracyanobutadienes as Colorimetric Sensors for Sulfide Ion in Aqueous Media
This project was partially supported by the National Nanotechnology Centre (NANOTEC), NSTDA, the Ministry of Science and Technology, Thailand, through its program of the Centre of Excellence Network. Q.N.N.P. thanks the Scholarship Program for ASEAN and Non–ASEAN Countries from Chulalongkorn University.
Abstract
Two diaryl derivatives of 1,1,4,4-tetracyanobuta-1,3-diene were synthesized for use as colorimetric ion sensors in aqueous media. The key synthetic step involved a [2+2]-cycloaddition/retro-cycloaddition between an electron-rich diarylethyne and electron-deficient tetracyanoethene. The compound bearing two sulfonamide groups showed good selectivity toward hydrogen sulfide ion, with a detection limit of 15.5 μM. The use of this sensor for the quantitative analysis of hydrogen sulfide ion in water samples was successfully demonstrated.
Key words
[2+2]-cycloaddition - polycyanobutadienes - sulfonamides - colorimetric sensors - hydrogen sulfide sensorSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1806-6258.
- Supporting Information
Publication History
Received: 27 January 2022
Accepted after revision: 23 March 2022
Accepted Manuscript online:
23 March 2022
Article published online:
22 April 2022
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- 33 The synthesis and characterizations of intermediate compounds 2–5 are described in the Supporting Information. N-{4-[2-(4-Aminophenyl)-3,3-dicyano-1-(dicyanomethylene)prop-2-en-1-yl]phenyl}methanesulfonamide (P1) and N,N′-[(1,1,4,4-Tetracyanobuta-1,3-diene-2,3-diyl)bis(4,1-phenylene)]dimethanesulfonamide (P2) 2,3-Bis(4-aminophenyl)buta-1,3-diene-1,1,4,4-tetracarbonitrile (5; 0.25 g, 0.74 mmol) was dissolved in CH2Cl2 (15 mL) and pyridine (1.0 mL) at RT. MeSO2Cl (0.13 mL, 1.64 mmol) was then slowly added dropwise from a syringe, and the mixture was allowed to react for 16 h. The crude product was extracted with EtOAc and 3 M aq HCl (×3). The crude residue was purified by column chromatography (silica gel, 1% MeOH in CH2Cl2) to give P1 as a dark-red solid [yield: 0.14 g; (45.5%)] and P2 as a brownish-yellow solid [yield: 0.12 g (33.3%)] P1 FTIR (ATR): 3465, 3368, 3232, 2218, 1601, 1484, 1448, 1335, 1145 cm–1. 1H NMR (500 MHz, acetone-d 6): δ = 9.49 (s, 0.5 H), 7.99 (d, J = 10 Hz, 2 H), 7.86 (d, J = 10 Hz, 2 H), 7.50 (d, J = 10 Hz, 2 H), 6.82 (d, J = 10 Hz, 2 H), 6.56 (s, 1 H), 3.21 (s, 3 H). 13C NMR (125 MHz, acetone-d 6): δ = 167.9, 164.8, 156.9, 145.6, 134.1, 132.5, 126.7, 119.1, 118.8, 115.3, 115.2, 114.7, 113.8, 113.3, 85.6, 75.9, 40.7. HRMS (MALDI-TOF): m/z [M + Na]+ calcd for C21H14N6NaO2S: 437.07966; found: 437.07920. P2 FT (ATR): 3253, 2229, 1602, 1506, 1460, 1331, 1245, 1146 cm–1. 1H NMR (500 MHz, acetone-d 6): δ = 9.51 (s, 2 H), 8.02 (d, J = 10 Hz, 4 H), 7.50 (d, J = 10 Hz, 4 H), 3.20 (s, 6 H). 13C NMR (125 MHz, acetone-d 6): δ = 166.1, 145.8, 132.7, 126.0, 119.1, 113.6, 113.3, 86.5, 40.8. HRMS (MALDI-TOF): m/z [M + 2Na – H]+ calcd for C22H15N6Na2O4S2: 537.03971; found: 537.03815.