Synthesis and Properties of Thiophene-Fused Thiopyrylium Salts

被引：7

作者：

Nagahora, Noriyoshi ^{[1
]}

Kitahara, Kana ^{[1
]}

Mizuhata, Yoshiyuki ^{[2
]}

Tokitoh, Norihiro ^{[2
]}

Shioji, Kosei ^{[1
]}

Okuma, Kentaro ^{[1
]}

机构：

[1] Fukuoka Univ, Fac Sci, Dept Chem, Fukuoka 8140180, Japan

[2] Kyoto Univ, Inst Chem Res, Uji, Kyoto 6110011, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 12期

基金：

日本学术振兴会;

关键词：

SOLID-STATE; CYCLIZATION; CRYSTAL; DYES;

D O I：

10.1021/acs.joc.0c00364

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new family of thiophene-fused thiopyrylium salts has been synthesized via Lewis-acid-induced Rieche formylation, followed by an intramolecular Friedel-Crafts cyclization of a series of diarylthioethers. Moreover, in the case of diarylthioethers that bear formyl groups, Lewis-acidpromoted intramolecular cyclizations afforded novel thiophene-fused bisthiopyrylium salts in good yield. The electronic structures of the new compounds were determined experimentally by NMR and UV-vis absorption spectroscopy and theoretically investigated by density functional theory calculations. The results of our examinations revealed effective conjugation of the pi-electrons over the entire linearly fused heteroacene framework.

引用

收藏

页码：7748 / 7756

页数：9

相关论文

共 26 条

[1]

Armarego W. L. F., 2017, PURIFICATION LAB CHE, DOI DOI 10.1016/B978-0-12-805457-4.50003-3

[2] DIRECT BRADSHER REACTION .2. SYNTHESIS OF PYRYLIUM AND THIOPYRYLIUM SALTS [J].

ASHBY, J ;

AYAD, M ;

METHCOHN, O .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (10) :1104-1107

[3] Polymethine materials with solid-state third-order optical susceptibilities suitable for all-optical signal-processing applications [J].

Barlow, Stephen ;

Bredas, Jean-Luc ;

Getmanenko, Yulia A. ;

Gieseking, Rebecca L. ;

Hales, Joel M. ;

Kim, Hyeongeu ;

Marder, Seth R. ;

Perry, Joseph W. ;

Risko, Chad ;

Zhang, Yadong .

MATERIALS HORIZONS, 2014, 1 (06) :577-581

[4] Nucleus-independent chemical shifts (NICS) as an aromaticity criterion [J].

Chen, ZF ;

Wannere, CS ;

Corminboeuf, C ;

Puchta, R ;

Schleyer, PV .

CHEMICAL REVIEWS, 2005, 105 (10) :3842-3888

[5] Effect of N-H•••S amide-thiolate hydrogen bonding on bond lengths in rubredoxin models [(CH3)3NCH2CONH2]2 [M(S2-o-xyl)2] [J].

Chung, WP ;

Dewan, JC ;

Tuckerman, M ;

Walters, MA .

INORGANICA CHIMICA ACTA, 1999, 291 (1-2) :388-394

[6] Polymethine Thiopyrylium Fluorophores with Absorption beyond 1000 nm for Biological Imaging in the Second Near-Infrared Subwindow [J].

Ding, Bingbing ;

Xiao, Yuling ;

Zhou, Hui ;

Zhang, Xiao ;

Qu, Chunrong ;

Xu, Fuchun ;

Deng, Zixin ;

Cheng, Zhen ;

Hong, Xuechuan .

JOURNAL OF MEDICINAL CHEMISTRY, 2019, 62 (04) :2049-2059

[7] Extended Bis(benzothia)quinodimethanes and Their Dications: From Singlet Diradicaloids to Isoelectronic Structures of Long Acenes [J].

Dong, Shaoqiang ;

Herng, Tun Seng ;

Gopalakrishna, Tullimilli Y. ;

Phan, Hoa ;

Lim, Zheng Long ;

Hu, Pan ;

Webster, Richard D. ;

Ding, Jun ;

Chi, Chunyan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (32) :9316-9320

[8]

Frisch M. J., 2016, Gaussian 16 Revision C. 01

[9] Effect of Bulky Substituents on Thiopyrylium Polymethine Aggregation in the Solid State: A Theoretical Evaluation of the Implications for All-Optical Switching Applications [J].

Gieseking, Rebecca L. ;

Mukhopadhyay, Sukrit ;

Risko, Chad ;

Marder, Seth R. ;

Bredas, Jean-Luc .

CHEMISTRY OF MATERIALS, 2014, 26 (22) :6439-6447

[10] Crystal structure of 6-(p-tolyl) benzo[b]naphtho[2,3-d]thiophene and of an orthorhombic polymorph of 7-phenylanthra[2,3-b]benzo[d]thiophene [J].

Gopinath, S. ;

Sethusankar, K. ;

Stoeckli-Evans, Helen ;

Rafiq, Muhamad ;

Mohanakrishnan, Arasambattu K. .

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2016, 72 :1310-+