A Pyrene-Embedded Molecular Nanotube with Donor-Acceptor Properties.
4 affiliations
- 1Department of Chemistry, Rice University, 6100 Main Street, Houston, Texas 77005, United States.
- 2Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, Pennsylvania 15260, United States.
- 3School of Engineering and Sciences, Tecnologico de Monterrey, Monterrey 64849, Mexico.
- 4Rice Advanced Materials Institute, Rice Sustainability Institute, Rice WaTER Institute, Rice University, Houston, Texas 77005, United States.
Abstract
Shape-persistent pyrene-embedded macrocycles remain scarce, and tubular conjugated molecules with intrinsic donor-acceptor (D-A) character have only recently emerged, largely within [n]-cyclo-para-phenylene-based systems. Here we introduce a structurally distinct pyrene-containing nanotube (Pyr4 ), synthesized through a templated approach using an n-pentyl resorcin[4]-arene, in which pyrene units and quinoxaline walls form an integrated D-A framework. Upon light excitation, Pyr4 displays behavior consistent with internal charge-transfer (ICT) between the pyrene donor (D) and the quinoxaline acceptor (A). The analogue with tolyl groups replacing pyrene (Tol4 ) shows markedly weaker D-A behavior. This assignment is supported by electrochemical studies, frontier molecular orbital analysis, and fluorescence solvatochromism, where emission shifts bathochromically by roughly 100 nm from 468 nm in hexane to 564 nm in DMSO. The fluorescence quantum yield (ϕf) falls with increasing solvent polarity, consistent with a stabilized charge-transfer state. In DCM, Pyr4 emits at 528 nm (ϕf = 0.2), red-shifted relative to previously reported pyrene-containing conjugated macrocycles.
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BibTeX
@article{mirzaei2026pyreneembedded,
title = {{A Pyrene-Embedded Molecular Nanotube with Donor-Acceptor Properties.}},
author = {Saber Mirzaei and M Saeed Mirzaei and Victor M Espinoza Castro and Marcelo Videa and Hormoz Khosravi and Raúl Hernández Sánchez},
journal = {Precision chemistry},
year = {2026},
month = sep,
doi = {10.1021/prechem.6c00084},
url = {https://europepmc.org/article/MED/42953273},
note = {CC BY-NC-ND},
}
RIS
TY - JOUR
TI - A Pyrene-Embedded Molecular Nanotube with Donor-Acceptor Properties.
AU - Saber Mirzaei
AU - M Saeed Mirzaei
AU - Victor M Espinoza Castro
AU - Marcelo Videa
AU - Hormoz Khosravi
AU - Raúl Hernández Sánchez
PY - 2026
DA - 2026/09/01
JO - Precision chemistry
DO - 10.1021/prechem.6c00084
UR - https://europepmc.org/article/MED/42953273
AB - Shape-persistent pyrene-embedded macrocycles remain scarce, and tubular conjugated molecules with intrinsic donor-acceptor (D-A) character have only recently emerged, largely within [n]-cyclo-para-phenylene-based systems. Here we introduce a structurally distinct pyrene-containing nanotube (Pyr4 ), synthesized through a templated approach using an n-pentyl resorcin[4]-arene, in which pyrene units and quinoxaline walls form an integrated D-A framework. Upon light excitation, Pyr4 displays behavior consistent with internal charge-transfer (ICT) between the pyrene donor (D) and the quinoxaline acceptor (A). The analogue with tolyl groups replacing pyrene (Tol4 ) shows markedly weaker D-A behavior. This assignment is supported by electrochemical studies, frontier molecular orbital analysis, and fluorescence solvatochromism, where emission shifts bathochromically by roughly 100 nm from 468 nm in hexane to 564 nm in DMSO. The fluorescence quantum yield (ϕf) falls with increasing solvent polarity, consistent with a stabilized charge-transfer state. In DCM, Pyr4 emits at 528 nm (ϕf = 0.2), red-shifted relative to previously reported pyrene-containing conjugated macrocycles.
SN - 2771-9316
ER -