Cyclopentannulated Dihydrotetraazapentacenes.

Robin HeckershoffSteffen MaierThomas WurmPhilipp BieggerKerstin BrödnerPetra KrämerMarvin T HoffmannLukas EberleJana SteinFrank RomingerMatthias RudolphJan FreudenbergAndreas DreuwA Stephen K HashmiUwe H F Bunz

Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2022)

The transition-metal-catalyzed cyclization of bissilylethynylated N,N'-dihydrotetraazapentacene (TIPS-TAP-H 2 ) into bissilylated cyclopenta[fg,qr]pentacenes is reported. Depending on the catalyst either none, one or two silyl groups migrate and change their positions in the formed five-membered rings. The optoelectronic properties are quite similar, whereas the packing motifs differ dramatically. Control experiments and quantum chemical calculations were performed to investigate the mechanism of the reaction and the selectivity of the silyl shift.

Keyphrases

transition metal
room temperature
molecular dynamics
density functional theory
monte carlo
ionic liquid
molecular dynamics simulations
highly efficient
reduced graphene oxide
metal organic framework
visible light
gold nanoparticles