Central substitution of azacalixphyrins: a strategy towards acidochromic NIR dyes

Physical Chemistry Chemical Physics : PCCP
Cloé AzariasDenis Jacquemin

Abstract

Azacalixphyrin derivatives constitute one of the most intriguing class of macrocyclic compounds. Indeed, these isostructural and isoelectronic analogues of porphyrins intensively absorb light up to the near infrared region, exist in several tautomeric forms and present a bis-zwitterionic structure, with a central dianionic core surrounded by positively-charged trimethine cyanines. However, control of the position of the absorption bands of azacalixphyrin remains an important challenge, as the experimental attempts reported to date have led to very modest auxochromic shifts only. Inspired by previous work demonstrating that the optical signatures of cyanines can be strongly modified by using central substituents, we have evaluated the validity of this strategy for azacalixphyrin considering several substituents positioned in symmetric or asymmetric manners around the core and linked through both single and double bonds, as well as several protonation states of the macrocycles. It turns out that bromine and dimethylamino substituents have a negligible or weak impact on the optical properties of azacalixphyrins with maximal redshifts smaller than 0.10 eV. The imino substitution induces strong geometrical deformations that counterb...Continue Reading

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Citations

Oct 17, 2018·Chemical Communications : Chem Comm·Lucien LavaudOlivier Siri
Dec 19, 2019·Chemical Communications : Chem Comm·Lucien LavaudOlivier Siri
Jan 5, 2019·The Journal of Organic Chemistry·Simon PascalOlivier Siri

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Gaussian16
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