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Baxter PN, Al Ouahabi A, Gisselbrecht JP, et al. Electronic, spectroscopic, and ion-sensing properties of a dehydro[m]pyrido[14]- and [15]annulene isomer library. J Org Chem. 2011;77(1):126-42doi: 10.1021/jo201595s.
Baxter, P. N., Al Ouahabi, A., Gisselbrecht, J. P., Brelot, L., & Varnek, A. (2012). Electronic, spectroscopic, and ion-sensing properties of a dehydro[m]pyrido[14]- and [15]annulene isomer library. The Journal of organic chemistry, 77(1), 126-42. https://doi.org/10.1021/jo201595s
Baxter, Paul N W, et al. "Electronic, spectroscopic, and ion-sensing properties of a dehydro[m]pyrido[14]- and [15]annulene isomer library." The Journal of organic chemistry vol. 77,1 (2012): 126-42. doi: https://doi.org/10.1021/jo201595s
Baxter PN, Al Ouahabi A, Gisselbrecht JP, Brelot L, Varnek A. Electronic, spectroscopic, and ion-sensing properties of a dehydro[m]pyrido[14]- and [15]annulene isomer library. J Org Chem. 2012 Jan 06;77(1):126-42. doi: 10.1021/jo201595s. Epub 2011 Dec 01. PMID: 22132764.
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J Org Chem. 2012 Jan 06;77(1):126-42. doi: 10.1021/jo201595s. Epub 2011 Dec 01.

Electronic, spectroscopic, and ion-sensing properties of a dehydro[m]pyrido[14]- and [15]annulene isomer library.

The Journal of organic chemistry

Paul N W Baxter, Abdelaziz Al Ouahabi, Jean-Paul Gisselbrecht, Lydia Brelot, Alexandre Varnek

Affiliations

  1. Institut Charles Sadron, UPR 22-CNRS, 23 rue du Loess, Strasbourg, France. [email protected]

PMID: 22132764 DOI: 10.1021/jo201595s

Abstract

An isomeric series of dehydro[m]pyrido[n]annulenes incorporating strained 1,4-buta-1,3-diyne units have been synthesized, where m = 2, n = 14 (1a-d); m = 2, n = 15 (2a,b); and m = 3, n = 15 (3). The number of pyridine rings and annulene ring π-electrons are denoted by m and n, respectively. The X-ray crystal structures of 1b and 1c confirmed their cyclic formulation. All macrocycles were found to be luminescent chromophores with differing isomer-dependent proton and metal ion-sensory emission responses, which appear collectively as analyte-specific color patterns. Within the series studied, 1a was singular in displaying the highest luminescence quantum yield and sharing the strongest emission energy and molar absorption changes upon protonation and Hg(II) binding. Spectroscopic and electrochemical results were supported by density functional theory calculations in showing 1a, 2a, and 3 to be low bandgap materials with lowest unoccupied molecular orbitals delocalized over the 1,4-di(pyridin-4-yl)buta-1,3-diyne bridges that provide a pathway for electronic communication between the nitrogens. Overall, the investigations suggest that 1a, 2a, and 3 would be excellent ligands for the construction of novel conjugated hybrid metallosupramolecular nanostructures, polymers, and ion-sensory systems.

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