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From the Decks to the Bridges: Optoelectronics in [2.2]Paracyclophane Chemistry
Author(s) -
Elacqua Elizabeth,
MacGillivray Leonard R.
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000930
Subject(s) - chromophore , chemistry , cyclophane , context (archaeology) , molecule , polymer , molecular wire , acceptor , charge (physics) , photochemistry , nanotechnology , organic chemistry , materials science , quantum mechanics , paleontology , physics , biology , condensed matter physics
Abstract In this microreview, we highlight optical properties of [2.2]paracyclophanes (pCps). We demonstrate how the spectroscopic properties that stem from the strained and π‐stacked structure have resulted in pCps being incorporated in materials science and polymer synthesis. As a result of chromophore substitution, internal charge transfer (ICT) between the two rings of the cyclophane core produce frameworks with unique optical properties. Deck‐substituted molecules and polymers have beensynthesized that possess donor and acceptor groups that affect internal charge transfer (ICT). We also demonstrate that bridge‐substituted [2.2]paracylophanes, although not well studied in this context, display unexpected optical properties owing to nonconventional ICT. A highlight is a recent templated solid‐state synthesis that affords a pCp that exhibits dramatic red‐shifted fluorescence.