Carbohelicenes and thiahelicene from phthalaldehydes through Perkin approach

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

Research output: Contribution to journalArticle

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

Fingerprint

o-Phthalaldehyde
Molecules
Benzene
Sulfur
Discrete Fourier transforms
Acetic Acid
Nanostructures
Carbon
heparinized hydrophilic polymer
3-thiophene acetic acid
anthracene

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Sarkar, Parantap ; Das, Bratin Kumar ; Chakraborty, Debashree ; Muthamma, Kashmitha. / Carbohelicenes and thiahelicene from phthalaldehydes through Perkin approach. In: Journal of Molecular Structure. 2019 ; Vol. 1195. pp. 309-314.
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Carbohelicenes and thiahelicene from phthalaldehydes through Perkin approach. / Sarkar, Parantap; Das, Bratin Kumar; Chakraborty, Debashree; Muthamma, Kashmitha.

In: Journal of Molecular Structure, Vol. 1195, 05.11.2019, p. 309-314.

Research output: Contribution to journalArticle

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