π-Extended S-Heterocyclic Naphthoquinodimethane with Dual Diradical and Dipolar Character

Weixiang Kueh; Xueliang Shi; Teng Wei Phua; Huilin Kueh; Yuan Cheng Liau; Chunyan Chi

doi:10.1021/acs.orglett.2c02188

π-Extended S-Heterocyclic Naphthoquinodimethane with Dual Diradical and Dipolar Character

Weixiang Kueh, Xueliang Shi, Teng Wei Phua, Huilin Kueh, Yuan Cheng Liau, Chunyan Chi

National University of Singapore

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

The 2,6-naphthoquinodimethane (2,6-NQDM) containing S-heterocyclic molecule 6-S was synthesized, and its dual open-shell diradical and dipolar characters were revealed via both experimental and theoretical studies. Unlike the shorter p-quinodimethane (p-QDM)-containing analogue 5-S, which possesses a closed-shell ground state (y0 = 0%) with small dipolar character, 6-S possesses enhanced dipolar character with a singlet diradical ground state (y0 = 23.3%) and a thermally accessible triplet excited state (ΔEST = -4.13 kcal/mol). Despite this, it displays good stability (t1/2 = 41days) under ambient air and light conditions due to its distinctive dipolar character and kinetic blocking of reactive sites.

Original language	English
Pages (from-to)	5935-5940
Number of pages	6
Journal	Organic Letters
Volume	24
Issue number	32
DOIs	https://doi.org/10.1021/acs.orglett.2c02188
State	Published - 19 Aug 2022
Externally published	Yes

Access to Document

10.1021/acs.orglett.2c02188

Cite this

@article{91fc37727ea44129a375f886edb359f1,

title = "π-Extended S-Heterocyclic Naphthoquinodimethane with Dual Diradical and Dipolar Character",

abstract = "The 2,6-naphthoquinodimethane (2,6-NQDM) containing S-heterocyclic molecule 6-S was synthesized, and its dual open-shell diradical and dipolar characters were revealed via both experimental and theoretical studies. Unlike the shorter p-quinodimethane (p-QDM)-containing analogue 5-S, which possesses a closed-shell ground state (y0 = 0\%) with small dipolar character, 6-S possesses enhanced dipolar character with a singlet diradical ground state (y0 = 23.3\%) and a thermally accessible triplet excited state (ΔEST = -4.13 kcal/mol). Despite this, it displays good stability (t1/2 = 41days) under ambient air and light conditions due to its distinctive dipolar character and kinetic blocking of reactive sites.",

author = "Weixiang Kueh and Xueliang Shi and Phua, \{Teng Wei\} and Huilin Kueh and Liau, \{Yuan Cheng\} and Chunyan Chi",

note = "Publisher Copyright: {\textcopyright} 2022 American Chemical Society.",

year = "2022",

month = aug,

day = "19",

doi = "10.1021/acs.orglett.2c02188",

language = "英语",

volume = "24",

pages = "5935--5940",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "32",

}

TY - JOUR

T1 - π-Extended S-Heterocyclic Naphthoquinodimethane with Dual Diradical and Dipolar Character

AU - Kueh, Weixiang

AU - Shi, Xueliang

AU - Phua, Teng Wei

AU - Kueh, Huilin

AU - Liau, Yuan Cheng

AU - Chi, Chunyan

PY - 2022/8/19

Y1 - 2022/8/19

N2 - The 2,6-naphthoquinodimethane (2,6-NQDM) containing S-heterocyclic molecule 6-S was synthesized, and its dual open-shell diradical and dipolar characters were revealed via both experimental and theoretical studies. Unlike the shorter p-quinodimethane (p-QDM)-containing analogue 5-S, which possesses a closed-shell ground state (y0 = 0%) with small dipolar character, 6-S possesses enhanced dipolar character with a singlet diradical ground state (y0 = 23.3%) and a thermally accessible triplet excited state (ΔEST = -4.13 kcal/mol). Despite this, it displays good stability (t1/2 = 41days) under ambient air and light conditions due to its distinctive dipolar character and kinetic blocking of reactive sites.

AB - The 2,6-naphthoquinodimethane (2,6-NQDM) containing S-heterocyclic molecule 6-S was synthesized, and its dual open-shell diradical and dipolar characters were revealed via both experimental and theoretical studies. Unlike the shorter p-quinodimethane (p-QDM)-containing analogue 5-S, which possesses a closed-shell ground state (y0 = 0%) with small dipolar character, 6-S possesses enhanced dipolar character with a singlet diradical ground state (y0 = 23.3%) and a thermally accessible triplet excited state (ΔEST = -4.13 kcal/mol). Despite this, it displays good stability (t1/2 = 41days) under ambient air and light conditions due to its distinctive dipolar character and kinetic blocking of reactive sites.

UR - https://www.scopus.com/pages/publications/85136158521

U2 - 10.1021/acs.orglett.2c02188

DO - 10.1021/acs.orglett.2c02188

M3 - 文章

C2 - 35938992

AN - SCOPUS:85136158521

SN - 1523-7060

VL - 24

SP - 5935

EP - 5940

JO - Organic Letters

JF - Organic Letters

IS - 32

ER -

π-Extended S-Heterocyclic Naphthoquinodimethane with Dual Diradical and Dipolar Character

Abstract

Access to Document

Other files and links

Fingerprint

Cite this