Abstract
Unsymmetrically fused porphyrins containing one or two naphthalimide subunits were prepared in modular syntheses relying on electron-rich and electron-poor pyrrole building blocks. These new chromophores show progressive changes in their electron-deficient character, while retaining comparably small optical and electrochemical band gaps. The intrinsic curvature and extended optical absorption of these systems make them of interest as mono- and difunctional components of multichromophoric assemblies.
Highlights
R yleneimides, most notably perylenediimides (PDIs), are one of the most important classes of organic dyes, with an exceptional scope of industrial and research applications.[1−5] Their electronic and self-assembly properties can be tuned by homologation of the rylene backbone,[3] modification of imide functionalities,[6] peripheral substitution,[1] and ring fusion.[7−9] Hybridization of ryleneimides with nonbenzenoid and heterocyclic moieties provides a versatile though still relatively unexplored route to structurally unique functional dyes
The electronic characteristics of such porphyrins can be tailored by juxtaposition of donor (D) and acceptor (A) units fused to the macrocyclic core (Scheme 1)
We envisaged that the optical band gaps, absorption profiles, and redox properties of such mixed D−A porphyrins might be affected by the ratio of D and A subunits and by the symmetry of the chromophore.[23−27] Systems containing imide functionalities are highly attractive as components for multichromophoric systems obtainable by covalent or supramolecular assembly
Summary
Seongsoo Kang − Department of Chemistry and Spectroscopy Laboratory for Functional π-Electronic Systems, Yonsei University, Seoul 03722, Korea. Piotr Chmielewski − Wydział Chemii, Uniwersytet Wrocławski, 50-383 Wrocław, Poland; orcid.org/0000-0002-25486110. Joanna Cybińska − Wydział Chemii, Uniwersytet Wrocławski, 50-383 Wrocław, Poland; PORT − Polski Osŕ odek Rozwoju Technologii, 54-066 Wrocław, Poland.
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