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Rajapaksha, Ishanka N. ; Wang, Jing ; Leszczynski, Jerzy , et al. Molecules,2023,28(13):4929. DOI: 10.3390/molecules28134929 PubMed ID: 37446594
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Abstract: NIR dyes have become popular for many applications, including biosensing and imaging. For this reason, the mol. switch mechanism of the xanthene dyes makes them useful for in vivo detection and imaging of bioanalytes. Our group has been designing NIR xanthene-based dyes by the donor-acceptor-donor approach; however, the equilibrium between their opened and closed forms varies depending on the donors and spacer. We synthesized donor-acceptor-donor NIR xanthene-based dyes with an alkyne spacer via the Sonogashira coupling reaction to investigate the effects of the alkyne spacer and the donors on the maximum absorption wavelength and the mol. switching (ring opening) process of the dyes. We evaluated the strength and nature of the donors and the presence and absence of the alkyne spacer on the properties of the dyes. It was shown that the alkyne spacer extended the conjugation of the dyes, leading to absorption wavelengths of longer values compared with the dyes without the alkyne group. In addition, strong charge transfer donors shifted the absorption wavelength towards the NIR region, while donors with strong π-donation resulted in xanthene dyes with a smaller equilibrium constant DFT/TDDFT calculations corroborated the exptl. data in most of the cases. Dye 2 containing the N,N-dimethylaniline group gave contrary results and is being further investigated.
Keywords: donor-acceptor-donor ; NIR dyes ; xanthene dyes ; amine donors ; alkyne spacers
Purchased from AmBeed: 589-87-7 ; 768-60-5 ; 201802-67-7 ; 57102-42-8 ; 17573-94-3 ; 1066-54-2 ; 205877-26-5 ; 28611-39-4 ; 262861-81-4 ; 1195931-66-8
CAS No. : | 17573-94-3 | MDL No. : | MFCD00168816 |
Formula : | C10H11N | Boiling Point : | - |
Linear Structure Formula : | HCC(C6H4N(CH3)2) | InChI Key : | ZWMAYLMVFSCMMS-UHFFFAOYSA-N |
M.W : | 145.20 | Pubchem ID : | 5191884 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H317-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | n-BuLi (2.5 M in hexanes) (11.80mL, 29.4 mmol) was added portionwise via syringe to a cold (-70 C)stirred solution of 4-ethynyl-N,N-dimethylaniline (4.27 g, 29.4 mmol) inanhydrous THF (30 mL) under N2. The cold solution was stirred for 30min and then <strong>[4038-15-7](2,4-dimethoxyphenyl)(4-methoxyphenyl)methanone</strong>(4.00 g, 14.7 mmol) was added in a single portion. The cooling bath wasremoved and the mixture stirred for 20 h at room temperature under N2.The reaction mixture was diluted with water (150 mL) and extractedwith EtOAc (3 × 75 mL). The combined organic extracts were washedwith water (150 mL), dried with anhydrous sodium sulfate and evaporatedto afford a brown oil. Elution from silica with 20% EtOAc/petroleumether afforded the title compound as an orange powder (0.87 g,85%); m.p. = 49-50 C; νmax (neat) 3506, 2932, 2834, 2217, 1605,1503, 1245, 1206, 1156, 1028, 816, 586 and 523 cm 1; 1H NMR (400MHz, CDCl3) δH 2.95 (6H, s, NMe2), 3.78 (3H, s, OMe), 3.80 (3H, s,OMe), 3.81 (3H, s, OMe), 4.77 (1H, s, OH), 6.44 (1H, dd, J = 8.6, 2.4 Hz,Ar-H), 6.51 (1H, d, J = 2.4 Hz, Ar-H), 6.58-6.62 (2H, m, Ar-H),6.84-6.88 (2H, m, Ar-H), 7.30-7.35 (3H, m, Ar-H), 7.49-7.53 (2H, m,Ar-H); 13C{1H} NMR (100 MHz, CDCl3) δC 40.24, 55.27, 55.41, 55.93,74.27, 87.39, 89.35, 100.16, 103.97, 109.97, 111.69, 113.17, 126.25,127.71, 129.22, 132.82, 137.45, 150.12, 157.94, 158.78, 160.58; HRMS(ESI) found [M+H]+ = 418.2002. C26H27NO4 requires [M+H]+ =418.2018. |
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