The Missing Member of the Partially O-Alkylated Resorcinarene Family: Synthesis and Conformation of Methyl Tetramethoxy Resorcinarene

Tero, Tiia-Riikka; Suhonen, Aku; Salorinne, Kirsi; Campos-Barbosa, Hélène; Nissinen, Maija

doi:10.1021/ol400118t

Final Draft

Katso/Avaa

597.1 Kb

Lataukset:

Show download details Hide download details

Tero, T.-R., Suhonen, A., Salorinne, K., Campos-Barbosa, H., & Nissinen, M. (2013). The Missing Member of the Partially O-Alkylated Resorcinarene Family: Synthesis and Conformation of Methyl Tetramethoxy Resorcinarene. Organic Letters, 15(5), 1096-1099. https://doi.org/10.1021/ol400118t

Julkaistu sarjassa

Organic Letters

Tekijät

Tero, Tiia-Riikka |

Suhonen, Aku |

Salorinne, Kirsi |

Campos-Barbosa, Hélène |

Nissinen, Maija

Päivämäärä

2013

Oppiaine

Orgaaninen kemia Nanoscience Center Organic Chemistry Nanoscience Center

Tekijänoikeudet

© 2013 American Chemical Society. This is a final draft version of an article whose final and definitive form has been published by ACS. Published in this repository with the kind permission of the publisher.

An improved Lewis acid catalyzed synthesis method for methyl tetramethoxy resorcinarene is described, which produced the missing lower rim methyl derivative of this partially O-alkylated resorcinarene family. Structural characterization by means of variable temperature NMR experiments and single crystal X-ray diffraction studies furthermore revealed that the resorcinarene core adopts different conformations in the solid state and in solution.

Julkaisija

American Chemical Society

ISSN Hae Julkaisufoorumista

1523-7060

Näytetään aineistoja, joilla on samankaltainen nimeke tai asiasanat.

A perspective to resorcinarene crowns

Tero, Tiia-Riikka; Nissinen, Maija (Elsevier, 2014)

In this report, we have summarized different synthesis methods of the resorcinarene crowns, discussed their structural and complexation properties together with the possible application aspects.
The Effect of Halogen Bonding on the Packing of Bromine Substituted Pyridine and Benzyl Functionalized Resorcinarene Tetrapodands in the Solid State

Tero, Tiia-Riikka; Salorinne, Kirsi; Nissinen, Maija (RSC publishing, 2012)

The synthesis and characterization of new bromine-substituted pyridine and benzyl functionalized tetramethoxy resorcinarene tetrapodands are described and their solid-state structural properties and interactions were studied ...
Cation binding resorcinarene bis-crowns: the effect of lower rim alkyl chain length on crystal packing and solid lipid nanoparticles

Helttunen, Kaisa; Salorinne, Kirsi; Barboza, Tahnie; Barbosa, Hélène Campos; Suhonen, Aku; Nissinen, Maija (Centre National de la Recherche Scientifique and The Royal Society of Chemistry, 2012)

A group of seven resorcinarene bis-crown ethers (CNBC5) with two polyether bridges at the upper rim and either propyl, butyl, pentyl, heptyl, nonyl, decyl or undecyl groups at the lower rim were synthesized and their binding ...
Correlating Solution‐ and Solid‐State Structures of Conformationally Flexible Resorcinarenes : Significance of a Sulfonyl Group in Intramolecular Self‐Inclusion

Pamuła, Małgorzata; Nissinen, Maija; Helttunen, Kaisa (Wiley-VCH Verlag, 2020)

In this study, the synthesis of tetramethoxy resorcinarene podands bearing p‐toluene arms connected by ‐SO3‐ (1) and ‐CH2O‐ (2) linkers is presented. In the solid state, the resorcinarene podand 1 forms an intramolecular ...
A conformationally adaptive macrocycle : conformational complexity and host–guest chemistry of zorb[4]arene

Yang, Liu-Pan; Lu, Song-Bo; Valkonen, Arto; Pan, Fangfang; Rissanen, Kari; Jiang, Wei (Beilstein-Institut zur Foerderung der Chemischen Wissenschaften, 2018)

Large amplitude conformational change is one of the features of biomolecular recognition and is also the basis for allosteric effects and signal transduction in functional biological systems. However, synthetic receptors ...