The reaction of anthracyl-α-hydroxyphosphonate with anthracene: Facile Access to diverse (bis)-anthracylphosphonates as a suitable source for useful extensive π-conjugates

Submitting author affiliation:
Birla Institute od Technology and Sciences, Pilani -Hyderabad Campus, Hyderabad, India

Beilstein Arch. 2019, 2019100.

Published 06 Sep 2019

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Molecular anthracene has been used as arene in the Friedel-Crafts (FC) type arylation reaction of anthracyl-α-hydroxyphosphonate in the presence of acid. A diverse product formation is observed, in which anthracene unit is found to be linked through its C1 position with α-C of phosphonate. Interestingly, the molecular conformation (X-ray structure) of this phosphonate reveals one of the bond angles of a tetrahedral carbon as 118o which is close to the C of sp2 character. The attacks from C1, C2 or C9 nucleophilic center of molecular anthracene to C10 atom of 9-anthrylphosphonate are also recognized. The diverse molecular structures are established spectroscopically. The bis-anthracyl compounds with a P-CH2 unit have been successfully utilized in Horner-Wadsworth-Emmons (HWE) reactions to afford extensive bis-anthracyl-linked π-conjugates. Thus, the electronically different substituent is attached to the system by varying the aldehydes. Among all these π-conjugates, the compound with three anthracyl core is noticed as a weak AIEgen (Aggregation-Induced emission active fluorogen).

Keywords: Anthracene, C-C bond formation, Phosphonate, π-conjugates, Aggregation-Induced emission

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Baig, M. Z. K.; Prusti, B.; Bhuin, S.; Chakravarty, M. Beilstein Arch. 2019, 2019100. doi:10.3762/bxiv.2019.100.v1

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