5 years ago

Toward Benzobis(thiadiazole)-based Diradicaloids

Toward Benzobis(thiadiazole)-based Diradicaloids
Jishan Wu, Hoa Phan, Tun Seng Herng, Yi Liu, Jun Ding, Tullimilli Y. Gopalakrishna
We theoretically predicted that acetylene-bridged benzo[1,2-c;4,5-c′]bis[1,2,5]thiadiazole (BBT) oligomers would show a quick increase of diradical character with the extension of chain length. To validate the hypothesis, six stable BBT-based diradicaloids were synthesized and fully characterized by X-ray crystallographic analysis and various spectroscopic measurements. Three of them showed prominent paramagnetic activity at elevated temperatures due to thermal population from the open-shell singlet ground state to triplet excited state. It was also found that substitution by electron-donating triphenylamine groups at the termini promoted the diradical character and reduced the singlet–triplet energy gap, and at the same time, resulted in intense near-infrared absorption. BBT-based diradicaloids! We theoretically and experimentally investigated the potential of using benzo[1,2-c;4,5-c′]bis[1,2,5]thiadiazole (BBT) as a general building block for stable open-shell singlet diradicaloids. The extension of π-conjugation and substitution by electron-donating groups result in an increase of diradical character and decrease of singlet–triplet energy gap.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/asia.201700732

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