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2026-09-30T10:09:54Z
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Alkoxy Substitution
Controls Columnar Organization
in Quinoxaline Cyclotetrabenzoin Macrocycles
Ashikur
Rahman Rabbi (25143100)
Sandipan Ghorai (15816058)
Asmita Shah (6333767)
Suraj Kumar Pathak (1560412)
Torsten Hegmann (572857)
Ognjen Š Miljanić (25143103)
Biophysics
Biochemistry
Space Science
Physical Sciences not elsewhere classified
Medicine
Evolutionary Biology
Chemical Sciences not elsewhere classified
Astronomical and Space Sciences not elsewhere classified
Cancer
Infectious Diseases
dimethyloctyl derivative displays
persistent quinoxaline macrocycles
columnar oblique liquid
diverse phase behavior
quinoxaline macrocycles
phase behavior
crystalline phase
substituted phenylenediamines
solid state
results demonstrate
macrocycle size
crystalline mesophase
branched 3
Shape-persistent quinoxaline macrocycles were synthesized
from
cyclotetrabenzil through condensations with substituted phenylenediamines.
Variation of peripheral alkoxy substituents systematically modulates
supramolecular organization in the solid state. Selected tetraalkoxy
macrocycles form ordered soft crystal columnar hexagonal phases, whereas
octaalkoxy derivatives exhibit more diverse phase behavior. Notably,
a branched 3,7-dimethyloctyl derivative displays a columnar oblique
liquid-crystalline phase. Single-crystal structures reveal layered
packing governed primarily by weak [C–H···O],
[C–H···N], and [C–H···π]
interactions. These results demonstrate that macrocycle size and side-chain
architecture influence columnar packing and phase behavior in quinoxaline
macrocycles, with the branched octaalkoxy derivative uniquely exhibiting
a liquid-crystalline mesophase.
2026-09-30T00:00:00Z
Text
Journal contribution
10.1021/acs.joc.6c00924.s001
https://figshare.com/articles/journal_contribution/Alkoxy_Substitution_Controls_Columnar_Organization_in_Quinoxaline_Cyclotetrabenzoin_Macrocycles/34031221
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