title: One-pot access to push-pull oligoenes by sequential [2 + 2] cycloaddition-retroelectrocyclization reactions.
abstract: The formal [2 + 2] cycloaddition-retroelectrocyclization reaction was employed as the key transformation to obtain donor-substituted, π-conjugated polycyanohexa-1,3,5-trienes (TCHTs and PCHTs) and polycyanoocta-1,3,5,7-tetraenes from donor-substituted tetracyanobuta-1,3-dienes (TCBDs) and electron-rich alkynes. These push-pull-substituted oligoene chromophores were also accessed in good yield from tetracyanoethylene and donor-substituted alkynes by using a one-pot protocol. All bis-(N,N-dialkylanilino) donor-substituted push-pull trienes and tetraenes showed better electron-accepting potency and lower HOMO-LUMO gaps than the corresponding TCBDs, as evidenced by optical and electrochemical studies.
authors: Laboratorium für Organische Chemie, ETH-Zürich , Hönggerberg, HCI, CH-8093 Zürich, Switzerland.
authors: Govindasamy
authors: G
authors: Jayamurugan
authors: Aaron D
authors: AD
authors: Finke
authors: Jean-Paul
authors: JP
authors: Gisselbrecht
authors: Corinne
authors: C
authors: Boudon
authors: W Bernd
authors: WB
authors: Schweizer
authors: François
authors: F
authors: Diederich