Chemistry Reference
In-Depth Information
Scheme 20 Preparation of [1,2-
b
]IF olefin 83a [
59
]
Scheme 21 Preparation of IF olefins 83b,c [
37
]
Scheme 22 Preparation of IF olefins 84a-c [
37
]
synthesized through Stille cross-coupling of stannane 75 with olefin 84b which
derived from dione 74 (Scheme
22
)[
37
].
Due to the highly electron deficient dicyanovinylene moiety, 83a-c and 84b,c
showed consistent stabilization of their HOMO and LUMO levels compared to 67d,
e, 73, and 76 by approximately 0.15 eV, and 0.6 eV, respectively, as well as a
lowered energy gap of approximately 0.5 eV. Furthermore, 83b,c and 84b,c
exhibited an approximate +0.6 V shift with respect to 67d,e, 73, and 76 in reduction
potentials. Solid state analysis of 84c found that the IF core maintains the bond
lengths of the three aromatic benzene rings found in
p
-terphenyl. Interestingly,
