10.1002/chem.201900312
Chemistry - A European Journal
FULL PAPER
Preparation of fluorescent organic nanoparticles
Experimental Section
2-CTPAN and 2,2’-CTPAN has been dissolved separately in THF at a
concentration of 1 mg/mL. Then 5 μL of 2-CTPAN and 8 μL of 2,2’-
CTPAN of the above solution have been added to a poor solvent (water)
to dilute the solution so that the final concentration of the solution
becomes 10-5 M. The final solutions have been stirred vigorously and
within 10 min of shaking the colloidal fluorescent organic nanoparticles
(FONPs) of 2-CTPAN and 2,2’-CTPAN has been formed.
Synthesis of compound 1 and 2
Compounds 1 and 2 have been prepared according to reported literature
procedure.[50,51]
Preparation of 2-(4-((9-butyl-9H-carbazol-3-yl)ethynyl)phenyl)-3,3-
diphenylacrylonitrile (2-CTPAN)
2-(4-bromophenyl)-3,3-diphenylacrylonitrile (500 mg, 1.39 mmol) was
dissolved in THF (20 mL) and Pd(PPh3)2Cl2 (30 mg, 0.04 mmol), PPh3
(36 mg, 0.14 mmol) and copper iodide (5 mg) added subsequently to it
under argon atmosphere. After 15 min of stirring at room temperature,
triethylamine (10 mL) was added to the reaction mixture and the stirring
was continued for further 30 min. After that, 9-butyl-3-ethynyl-9H-
carbazole (340 mg, 1.39 mmol) was added to it and the reaction mixture
was heated at 80 0C for 6 h. After completion of the reaction all volatile
materials were removed under vacuum and the residue was extracted
with ethyl acetate (3 × 20 mL). The crude product was purified using
column chromatography (silica gel/ethyl acetate : petroleum ether, 1:4)
afforded 2-CTPAN (522 mg, Yield = 72%) as a light yellow solid. 1H NMR
(500 MHz, CDCl3): δ 8.27 (s, 1H), 8.11 (d, J = 7.5, 1H), 7.61 (s, 1H),
7.50-7.37 (m, 10H), 7.29-7.22 (m, 6H), 7.06 (t, J = 6.6, 2H), 4.33 (t, J =
7.2, 2H), 1.87 (q, J = 7.2, 2H), 1.43 (q, J = 7.3, 2H), 0.96 (t, J = 7.3, 3H).
13C NMR (100 MHz, CDCl3): δ 158.15, 140.98, 140.50, 140.39, 139.14,
134.24, 131.54, 130.92, 130.10, 129.80, 129.37, 129.30, 128.61, 128.53,
126.29, 124.25, 124.17, 123.04, 122.56, 120.64, 120.03, 119.54, 112.95,
111.29, 109.10, 108.91, 92.73, 87.30, 43.12, 31.22, 20.66, 13.98. HRMS
(ESI, m/z): calcd for C39H30N2Na (M+Na)+, 549.2307; found, 549.2305.
Acknowledgements
S. M. and C. P. are thankful to the University Grant Commission
(UGC), India for providing the research fellowship.
Keywords: AIEE • self-assembly • solvent dependent
nanoprobes • staircase-shaped supramolecular association •
bio-imaging
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