Cambiarenes: Single-Step Synthesis and Selective Zwitterion Binding of a Clip-Shaped Macrocycle with a Redox-Active Core

Riley J. Petersen; Brett J. Rozeboom; Shalisa M. Oburn; Nolan J. Blythe; Tanner L. Rathje; Javier A. Luna; Steven K. Kibby; Emily A. O'Brien; Kayleigh G. Rohr; Joshua R. Carpenter; Taylor L. Sanders; Andrew M. Johnson; Kristin M. Hutchins; Scott K. Shaw; Leonard R. MacGillivray; Jay Wm Wackerly

doi:10.1002/chem.201904852

Cambiarenes: Single-Step Synthesis and Selective Zwitterion Binding of a Clip-Shaped Macrocycle with a Redox-Active Core

Riley J. Petersen, Brett J. Rozeboom, Shalisa M. Oburn, Nolan J. Blythe, Tanner L. Rathje, Javier A. Luna, Steven K. Kibby, Emily A. O'Brien, Kayleigh G. Rohr, Joshua R. Carpenter, Taylor L. Sanders, Andrew M. Johnson, Kristin M. Hutchins, Scott K. Shaw, Leonard R. MacGillivray, Jay Wm Wackerly

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

Abstract

A novel macrocyclic host molecule was synthesized that forms in a single step from commercially available starting materials. The core of the macrocycle backbone possesses two quinone rings and, thus, it is redox-active. Host–guest binding involving the clip-shaped cavity indicates selective binding of pyridine N-oxides based on the electron density of and steric bulk around the anionic oxygen.

Original language	English
Pages (from-to)	1928-1930
Number of pages	3
Journal	Chemistry - A European Journal
Volume	26
Issue number	9
DOIs	https://doi.org/10.1002/chem.201904852
State	Published - Feb 11 2020

Keywords

host–guest systems
macrocycles
quinones
redox chemistry
supramolecular chemistry

Access to Document

10.1002/chem.201904852

Link to publication in Scopus

Fingerprint Dive into the research topics of 'Cambiarenes: Single-Step Synthesis and Selective Zwitterion Binding of a Clip-Shaped Macrocycle with a Redox-Active Core'. Together they form a unique fingerprint.

Cite this

Petersen, R. J., Rozeboom, B. J., Oburn, S. M., Blythe, N. J., Rathje, T. L., Luna, J. A., Kibby, S. K., O'Brien, E. A., Rohr, K. G., Carpenter, J. R., Sanders, T. L., Johnson, A. M., Hutchins, K. M., Shaw, S. K., MacGillivray, L. R., & Wackerly, J. W. (2020). Cambiarenes: Single-Step Synthesis and Selective Zwitterion Binding of a Clip-Shaped Macrocycle with a Redox-Active Core. Chemistry - A European Journal, 26(9), 1928-1930. https://doi.org/10.1002/chem.201904852

Petersen, Riley J. ; Rozeboom, Brett J. ; Oburn, Shalisa M. ; Blythe, Nolan J. ; Rathje, Tanner L. ; Luna, Javier A. ; Kibby, Steven K. ; O'Brien, Emily A. ; Rohr, Kayleigh G. ; Carpenter, Joshua R. ; Sanders, Taylor L. ; Johnson, Andrew M. ; Hutchins, Kristin M. ; Shaw, Scott K. ; MacGillivray, Leonard R. ; Wackerly, Jay Wm. / Cambiarenes : Single-Step Synthesis and Selective Zwitterion Binding of a Clip-Shaped Macrocycle with a Redox-Active Core. In: Chemistry - A European Journal. 2020 ; Vol. 26, No. 9. pp. 1928-1930.

@article{b125eee93b3140869e5e86346bfe3478,

title = "Cambiarenes: Single-Step Synthesis and Selective Zwitterion Binding of a Clip-Shaped Macrocycle with a Redox-Active Core",

abstract = "A novel macrocyclic host molecule was synthesized that forms in a single step from commercially available starting materials. The core of the macrocycle backbone possesses two quinone rings and, thus, it is redox-active. Host–guest binding involving the clip-shaped cavity indicates selective binding of pyridine N-oxides based on the electron density of and steric bulk around the anionic oxygen.",

keywords = "host–guest systems, macrocycles, quinones, redox chemistry, supramolecular chemistry",

author = "Petersen, {Riley J.} and Rozeboom, {Brett J.} and Oburn, {Shalisa M.} and Blythe, {Nolan J.} and Rathje, {Tanner L.} and Luna, {Javier A.} and Kibby, {Steven K.} and O'Brien, {Emily A.} and Rohr, {Kayleigh G.} and Carpenter, {Joshua R.} and Sanders, {Taylor L.} and Johnson, {Andrew M.} and Hutchins, {Kristin M.} and Shaw, {Scott K.} and MacGillivray, {Leonard R.} and Wackerly, {Jay Wm}",

year = "2020",

month = feb,

day = "11",

doi = "10.1002/chem.201904852",

language = "English",

volume = "26",

pages = "1928--1930",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

number = "9",

}

Petersen, RJ, Rozeboom, BJ, Oburn, SM, Blythe, NJ, Rathje, TL, Luna, JA, Kibby, SK, O'Brien, EA, Rohr, KG, Carpenter, JR, Sanders, TL, Johnson, AM, Hutchins, KM, Shaw, SK, MacGillivray, LR & Wackerly, JW 2020, 'Cambiarenes: Single-Step Synthesis and Selective Zwitterion Binding of a Clip-Shaped Macrocycle with a Redox-Active Core', Chemistry - A European Journal, vol. 26, no. 9, pp. 1928-1930. https://doi.org/10.1002/chem.201904852

Cambiarenes : Single-Step Synthesis and Selective Zwitterion Binding of a Clip-Shaped Macrocycle with a Redox-Active Core. / Petersen, Riley J.; Rozeboom, Brett J.; Oburn, Shalisa M.; Blythe, Nolan J.; Rathje, Tanner L.; Luna, Javier A.; Kibby, Steven K.; O'Brien, Emily A.; Rohr, Kayleigh G.; Carpenter, Joshua R.; Sanders, Taylor L.; Johnson, Andrew M.; Hutchins, Kristin M.; Shaw, Scott K.; MacGillivray, Leonard R.; Wackerly, Jay Wm.

In: Chemistry - A European Journal, Vol. 26, No. 9, 11.02.2020, p. 1928-1930.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Cambiarenes

T2 - Single-Step Synthesis and Selective Zwitterion Binding of a Clip-Shaped Macrocycle with a Redox-Active Core

AU - Petersen, Riley J.

AU - Rozeboom, Brett J.

AU - Oburn, Shalisa M.

AU - Blythe, Nolan J.

AU - Rathje, Tanner L.

AU - Luna, Javier A.

AU - Kibby, Steven K.

AU - O'Brien, Emily A.

AU - Rohr, Kayleigh G.

AU - Carpenter, Joshua R.

AU - Sanders, Taylor L.

AU - Johnson, Andrew M.

AU - Hutchins, Kristin M.

AU - Shaw, Scott K.

AU - MacGillivray, Leonard R.

AU - Wackerly, Jay Wm

PY - 2020/2/11

Y1 - 2020/2/11

N2 - A novel macrocyclic host molecule was synthesized that forms in a single step from commercially available starting materials. The core of the macrocycle backbone possesses two quinone rings and, thus, it is redox-active. Host–guest binding involving the clip-shaped cavity indicates selective binding of pyridine N-oxides based on the electron density of and steric bulk around the anionic oxygen.

AB - A novel macrocyclic host molecule was synthesized that forms in a single step from commercially available starting materials. The core of the macrocycle backbone possesses two quinone rings and, thus, it is redox-active. Host–guest binding involving the clip-shaped cavity indicates selective binding of pyridine N-oxides based on the electron density of and steric bulk around the anionic oxygen.

KW - host–guest systems

KW - macrocycles

KW - quinones

KW - redox chemistry

KW - supramolecular chemistry

UR - http://www.scopus.com/inward/record.url?scp=85078876290&partnerID=8YFLogxK

U2 - 10.1002/chem.201904852

DO - 10.1002/chem.201904852

M3 - Article

C2 - 31696566

AN - SCOPUS:85078876290

VL - 26

SP - 1928

EP - 1930

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 9

ER -