Twisted tethered tolanes: unanticipated long-lived phosphorescence at 77 K.
Influencing the communication within a conjugated system as diphenylacetylene is a challenging subject in molecular electronics. Some examples of twisted tolanes are known, where high twists have been achieved in the solid state by steric encumbrance. The insertion of a spacer system is an alternative way to tailor rotation. Only a few examples of such tethered tolanes exist, and they all suffer from small twist angles (<35°). We report on tolanophanes containing a malonyl tether, where twist angles of almost 80° were reached. Long-lived phosphorescence (4 s at 77 K) was recorded, and quantum-chemical calculations were performed to confirm the experimental results.
Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
Sebastian
S
Menning
Maximilian
M
Krämer
Benjamin A
BA
Coombs
Frank
F
Rominger
Andrew
A
Beeby
Andreas
A
Dreuw
Uwe H F
UH
Bunz
D018360:Crystallography, X-Ray; D005453:Fluorescence; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011789:Quantum Theory; D013696:Temperature
D007659:Ketones