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1 article(s) from Wessig, Pablo

Articulated rods – a novel class of molecular rods based on oligospiroketals (OSK)

Pablo Wessig,
Roswitha Merkel and
Peter Müller

Beilstein J. Org. Chem. 2015, 11, 74–84, doi:10.3762/bjoc.11.11

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Graphical Abstract

Figure 1: Typical OSK rod A with solubility enhancing sleeve (D) and building blocks B,C,E.

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Figure 2: Fundamental structure of articulated rods (blue = legs, red = joint, green = terminal functionaliti...

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Figure 3: Synthetic strategy towards articulated rods.

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Scheme 1: Synthesis of building block 8 (i: trimethylsilylpropargyl-4-nitrophenylcarbonate. ii: Dess–Martin-p...

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Scheme 2: Synthesis of articulated rod 11 (i: CBr₄, PPh₃, NaN₃. ii: K₂CO₃/MeOH. iii: Cu/C DCM/MeOH 1:1, cat. ...

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Scheme 3: Sequential deprotection of 11 and synthesis of triple articulated rod 14 (i: K₂CO₃/MeOH. ii: CBr₄/P...

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Scheme 4: Synthesis of articulated rods 23–25 with increased solubility (i: 4-hydroxypiperidine, DCC, HOBt. i...

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Scheme 5: Macrocyclization of articulated rod 25.

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Scheme 6: Synthesis of building blocks 27–29 (i: 1. pyrene-1-ylacetic acid, DCC/DMAP, 68%; 2. Dess–Martin per...

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Scheme 7: Synthesis of articulated rods 32a–c (i: NaH, TMSCl, TMSOTf. ii: Cu/C, Et₃N).

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Scheme 8: Synthesis of articulated rods 33, 34 and 36.

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Scheme 9: Synthesis of articulated rod 39 (i: cinnamoyl chloride, DMAP, pyridine. ii: DMF 120 °C).

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Scheme 10: Synthesis of functionalized articulated rod 43 (i: PYBOP, Et₃N. ii: KOH, H₂O. iii: 32c, quant.).

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Scheme 11: Stretched-folded equilibrium of pyrene labelled AR 32a.

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Figure 4: Fluorescence spectra of AR 32a in EPA at different temperatures (c = 5·10⁻⁶ mol/L).

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Figure 5: Monomer–excimer ratio I_M/I_EX of the fluorescence of 32a depending on solvent viscosity (DCE = 1,2-d...

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Figure 6: Monomer–excimer ratio I_M/I_EX of the fluorescence of 32a depending on the addition of cyclodextrines...

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Scheme 12: Formation of pseudorotaxanes from AR 32a and cyclodextrines.

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Figure 7: Influence of Triton X-100 on the fluorescence spectra of 32a in aqueous solution. 32a was added fro...

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Figure 8: Comparison of photochemical reactivity of 32b, 33a, 39 (left). Irradiation UV spectrum of 32b in AC...

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Published 16 Jan 2015

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