Wydział Chemii

Halina Zhylitskaya

Joanna Cybińska

Piotr J. Chmielewski

Tadeusz Lis

Marcin Stępień

2016

Journal of the American Chemical Society

138

11390-11398

10.1021/jacs.6b07826

Naukowa

Angielski

Artykuł

A family of bandgap-tunable pyrroles structurally related to rylene dyes was computationally designed and prepared using robust, easily scalable chemistry. These pyrroles show highly variable fluorescence properties and can be used as building blocks for the synthesis of electron-deficient oligopyrroles. The latter application is demonstrated through the development of π-extended porphyrins containing naphthalenediamide or naphthalenediimide units. These new macrocycles exhibit simultaneously tunable visible and near-IR absorptions, an ability to accept up to 8 electrons via electrochemical reduction, and high internal molecular free volumes. When chemically reduced under inert conditions, the most electron-deficient of these macrocycles revealed reversible formation of eight charged states, characterized by remarkably red-shifted optical absorptions, extending beyond 2200 nm. Such features make these oligopyrroles of interest as functional chromophores, charge-storage materials, and tectons for crystal engineering.

http://dx.doi.org/10.1021/jacs.6b07826

https://www.acs.org/content/acs/en.html