Carbohelicenes and thiahelicene from phthalaldehydes through Perkin approach

Parantap Sarkar, Bratin Kumar Das, Debashree Chakraborty, Kashmitha Muthamma

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Synthesis and structural features of helical nanographene molecules comprising of seven benzene rings are examined. Thus dibutyl-dicarboxylate functional [7]helicene and its two regioisomers, dinaphtho[1,2–a:1′,2′–h]anthracene and naphtho[2,1–c]pentahelicene, have been synthesized in two steps through Perkin approach using napthalene-2-acetic acid and ortho- or meta-phthalaldehydes. The feasibility of this approach to construct sulfur doped twisted dithiaarenes is also investigated by using thiophene-3-acetic acid. While dithiaarenes from meta-phthalaldehyde remains challenging, synthesis and characterization of planar anthra[1,2–b:5,6–b']dithiophene and twisted 1,12-dithiapentahelicene is successful from ortho-phthalaldehyde. Conformational analysis with DFT calculation shows unique helicity preference in such doubly helical carbon nanostructures. Absorption and emission behavior of these π-extended molecules shows enhanced conjugation.

Original languageEnglish
Pages (from-to)309-314
Number of pages6
JournalJournal of Molecular Structure
Volume1195
DOIs
Publication statusPublished - 05-11-2019

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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