O,O′-Disubstituted N,N′-Dihydroxynaphthalenediimides (DHNDI): First Principles Designed Organic Building Blocks for Materials Science
N,N′-Disubstituted naphthalenediimides (NDIs), planar, electron-deficient building blocks, play an important role in materials and biological sciences. Naphthalene core substituents control the HOMO and LUMO energies, whereas the N-alkyl or aryl substituents affect the solubility, aggregation, and p...
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Published in | Organic letters Vol. 13; no. 20; pp. 5432 - 5435 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
21.10.2011
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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Summary: | N,N′-Disubstituted naphthalenediimides (NDIs), planar, electron-deficient building blocks, play an important role in materials and biological sciences. Naphthalene core substituents control the HOMO and LUMO energies, whereas the N-alkyl or aryl substituents affect the solubility, aggregation, and packing propensity in condensed phases. N,N′-Dihydroxynaphthalenediimide (DHNDI) allows expanding the chemical diversity by O-alkylation, acylation, or sulfonylation; these derivatives also allow fine-tuning of the HOMO/LUMO levels. The synthesis, UV–vis, electrochemical, solid state, and computational prediction of the properties of such derivatives are presented. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/ol201906z |