2016
DOI: 10.1039/c5sc04218f
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Towards pi-extended cycloparaphenylenes as seeds for CNT growth: investigating strain relieving ring-openings and rearrangements

Abstract: Upon exposure to Scholl reaction conditions, cycloparaphenylenes undergo facile strain-relieving rearrangements and ring-openings.

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Cited by 85 publications
(84 citation statements)
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“…Despite molecular strain, nanohoops are only reactive under forcing reaction conditions. [35] The inherent attributes provided by the nanohoop structure highlight their potential as new fluorophores for biological imaging. Despite this exciting proposition, to date, there are no reported biological investigations of these small molecular slices of carbon nanotubes.…”
Section: Introductionmentioning
confidence: 99%
“…Despite molecular strain, nanohoops are only reactive under forcing reaction conditions. [35] The inherent attributes provided by the nanohoop structure highlight their potential as new fluorophores for biological imaging. Despite this exciting proposition, to date, there are no reported biological investigations of these small molecular slices of carbon nanotubes.…”
Section: Introductionmentioning
confidence: 99%
“…1 H NMR chemical shifts in CDCl 3 are reported in parts per million (ppm) downfield from tetramethylsilane. 13 C NMR chemical shifts in CDCl 3 are referred to the solvent signals as 77.0 ppm. The peak assignment of 1 H and 13 C NMR spectra reported was accomplished by HH COSY, DEPT, HMQC, and HMBC experiments.…”
Section: Methodsmentioning
confidence: 99%
“…The organic layer was dried over MgSO 4 and concentrated under reduced pressure. The residue was purified by column chromatography on Al 2 O 3 with dichloromethane/hexane (1:6) ; UVvis (CH 2 Cl 2 ): (log ¾) = 289 (4.71), 339 sh (4.04) nm; 1 H NMR (500 MHz, CDCl 3 , RT): ¤ = 7.63 (ddd, J = 1.9, 1.9, 0.4 Hz, 1H, 2¤-H), 7.58 (d,J = 8.6 Hz,2H,2,7.54 (d,J = 8.6 Hz,2H,3,7.41 (ddd,J = 7.7,1.9,1.9 Hz, 1H, 4¤-H), 7.39 (ddd, J = 7.7, 6.9, 0.4 Hz, 1H, 5¤-H), 7.34 (ddd, J = 6.9, 1.9, 1.9 Hz, 1H, 6¤-H), 3.79 (q, J = 7.1 Hz, 4H, 3¤-N 3 Et 2 ), 1.28 (t, J = 7.1 Hz, 6H, 3¤-N 3 Et 2 ), 1.14 (s, 21H, TIPS) ppm; 13 C NMR (125 MHz, CDCl 3 , RT): ¤ = 151.77 (C-3¤), 141.27 (C-1), 140.97 (C-1¤), 132.34 (C-3,5) Si: C,74.77;H,9.06;N,9.69. Found: C,74.36;H,8.64;N,9.67.…”
Section: [(3¤-aminobiphenyl-4-yl)ethynyl]triisopropylsilane (8)mentioning
confidence: 99%
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