Correction to “Adaptation in Constitutional Dynamic Libraries and

Scheme 5. Weighted Graph Representation of the Square CDN of E-1A1C, 1A3C, 2A1C, and 2A3C Constituents a a. The addition of metal cation is represente...
13 downloads 9 Views 1MB Size
Addition/Correction Cite This: J. Am. Chem. Soc. XXXX, XXX, XXX−XXX

pubs.acs.org/JACS

Correction to “Adaptation in Constitutional Dynamic Libraries and Networks, Switching between Orthogonal Metalloselection and Photoselection Processes” Ghislaine Vantomme, Shimei Jiang, and Jean-Marie Lehn* J. Am. Chem. Soc., 2014, 136, 9509−9518. DOI: 10.1021/ja504813r depends on the pH of the solution. The additional results coming from our further studies will be published elsewhere. As a consequence of these corrections, Scheme 4 and Scheme 5 should be replaced with the revised versions shown here. We apologize to the reader for any inconvenience. We thank Dr. Guangwen Men for performing a series of complementary measurements.

Pages 9514 and 9515. In this Article we reported on the adaptation of constitutional dynamic networks of acylhydrazones by metalloselection and photoselection. Additional experiments indicated that the metalloselection described on page 9514, right column, second full paragraph (with reference to Schemes 4 and 5), could not be reproduced. The addition of zinc triflate (5 mM) to the DCL of acylhydrazones 1A1C, 1A3C, 2A1C, and 2A3C (10 mM each) in 3:2 acetonitrile/water solution followed by overnight heating at 60 °C gives the distribution 27/23/21/25% for the constituents 1A1C/1A3C/2A1C/2A3C respectively, with 4% hydrolysis, resulting in complexation of 1A3C in the form of Zn(1A3C)2 and of 1A1C in the form of both Zn(1A1C)2 (24%) and the isomer Z-1A1C (3%) with no selection. It did not change on further heating. These percentages indicate no adaptation response of the DCL to the addition of zinc triflate. The difference in these results may come from the polarizability of the N−H bond that changes upon complexation of 1A1C to zinc cation, and

Scheme 4. Adaptation of the DCL of Four Acylhydrazone Constituents E-1A1C, 1A3C, 2A1C, and 2A3C by Modification of the Distributions under (Left) Addition of Zinc(II) Metal Cation with Formation of the Complexes Zn(1A3C)2 and Zn(1A1C)2 and (Right) Photoselection by Photoisomerization of E-1A1C into Z-1A1C on Light Irradiation and Distribution of the Constituents of the DCL before (Middle) and after Metal Ion Addition (Bottom Left) and after Photoselection (Bottom Right)a

a For clarity, only the structures of the major components are represented on the right and left hand sides. For the CDN representation, see Scheme 5. Error on % determination: ∼5%.

© XXXX American Chemical Society

A

DOI: 10.1021/jacs.7b13425 J. Am. Chem. Soc. XXXX, XXX, XXX−XXX

Journal of the American Chemical Society

Addition/Correction

Scheme 5. Weighted Graph Representation of the Square CDN of E-1A1C, 1A3C, 2A1C, and 2A3C Constituentsa

a

The addition of metal cation is represented by the complexation to form Zn(1A3C)2 and Zn(1A1C)2 with no selection (left). The adaptation to photoirradiation, photoselection, is represented by the selection and amplification of the Z-1A1C and 2A3C diagonal (right). The diagonals and edges of the square link respectively agonistic (+) and antagonistic (−) constituents.

B

DOI: 10.1021/jacs.7b13425 J. Am. Chem. Soc. XXXX, XXX, XXX−XXX