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Planar Benzo[1,2- b:4,5- B']dithiophene Derivatives Decorated With Nitronyl and Imino Nitroxides

Planar Benzo[1,2- b:4,5- B']dithiophene Derivatives Decorated With Nitronyl and Imino Nitroxides

Kubandiran Kolanji, Lars Postulka, Bernd Wolf, Michael Lang, Dieter Schollmeyer, Martin Baumgarten

J Org Chem. 2019 Jan 4;84(1):140-149.

PMID: 30421918

Abstract:

Four weakly antiferromagnetic interacting biradicals of benzo[1,2- b:4,5- b']dithiophene (BDT) and BDT extended with two thiophenes (BDTTh2) linked with nitronyl and imino nitroxides (NN and IN) as BDT-NN, BDT-IN, BDTTh2-NN, and BDTTh2-IN were designed, synthesized, and characterized. Short intermolecular π-π distances were found (3.42 Å) for BDT-NN, whereas larger ones were found for BDT-IN (3.54 Å) and BDTTh2-NN (3.67 Å), respectively. Intramolecular magnetic interaction ( Jintra,exp/ kB) of BDT-NN (-26 K) is much larger than for BDT-IN (-5.3 K), while it is reduced for the dithiophene-extended molecule BDTTh2-NN (-2.3 K). Intermolecular interactions ( zJinter,exp/ kB) of BDT-NN (-6.5 K) and BDT-IN (-6.0 K) are stronger than for BDTTh2-NN (-4.6 K). Such large intermolecular couplings resulting from good π-stacking mark BDT-IN and BDTTh2-NN as promising crystalline materials with similar sized Jintra and Jinter. In addition, we also extracted a coupling within the chain of Jchain/ kB = -2.2 K and a coupling between the chains of zJinterchain = -1.5 K for BDTTh2-NN by a Heisenberg chain model. Intra- and intermolecular interactions and spin densities were examined by DFT studies.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1134942203	2,6-Ditolylbenzo[1,2-b:4,5-b′]dithiophene		1134942-20-3	Price

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