TY - JOUR
T1 - Carbohelicenes and thiahelicene from phthalaldehydes through Perkin approach
AU - Sarkar, Parantap
AU - Das, Bratin Kumar
AU - Chakraborty, Debashree
AU - Muthamma, Kashmitha
PY - 2019/11/5
Y1 - 2019/11/5
N2 - 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.
AB - 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.
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U2 - 10.1016/j.molstruc.2019.05.118
DO - 10.1016/j.molstruc.2019.05.118
M3 - Article
AN - SCOPUS:85067244640
SN - 0022-2860
VL - 1195
SP - 309
EP - 314
JO - Journal of Molecular Structure
JF - Journal of Molecular Structure
ER -