Thiophene-fused aromatic belts

Abstract Aromatic belts, ultrashort carbon nanotubes, and related structures, are emerging molecular entities in the fields of organic electronics and supramolecular chemistry owing to their structural rigidity, fully fused π-conjugation, and well-defined cavity. Synthesis of aromatic belts with emb...

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Main Authors: Hiroki Shudo, Philipp Wiesener, Elena Kolodzeiski, Kiichi Mizukami, Daiki Imoto, Harry Mönig, Saeed Amirjalayer, Hirotoshi Sakamoto, Henning Klaasen, Bart Jan Ravoo, Nobuo Kimizuka, Akiko Yagi, Kenichiro Itami
Format: Article
Language:English
Published: Nature Portfolio 2025-02-01
Series:Nature Communications
Online Access:https://doi.org/10.1038/s41467-025-55896-w
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author Hiroki Shudo
Philipp Wiesener
Elena Kolodzeiski
Kiichi Mizukami
Daiki Imoto
Harry Mönig
Saeed Amirjalayer
Hirotoshi Sakamoto
Henning Klaasen
Bart Jan Ravoo
Nobuo Kimizuka
Akiko Yagi
Kenichiro Itami
author_facet Hiroki Shudo
Philipp Wiesener
Elena Kolodzeiski
Kiichi Mizukami
Daiki Imoto
Harry Mönig
Saeed Amirjalayer
Hirotoshi Sakamoto
Henning Klaasen
Bart Jan Ravoo
Nobuo Kimizuka
Akiko Yagi
Kenichiro Itami
author_sort Hiroki Shudo
collection DOAJ
description Abstract Aromatic belts, ultrashort carbon nanotubes, and related structures, are emerging molecular entities in the fields of organic electronics and supramolecular chemistry owing to their structural rigidity, fully fused π-conjugation, and well-defined cavity. Synthesis of aromatic belts with embedded thiophene structures, which manifest significant optoelectronic and conductive properties, has not yet been achieved. Herein, we report the synthesis of thiophene-fused aromatic belts (thiophene belts) via one-step sulfur cross-linking reaction of partially fluorinated cycloparaphenylenes. Their structural features, including unidirectional columnar stacking with high dipole moment in crystals, two-dimensional layer assembly on metal surfaces, and photophysical properties, such as long-lifetime phosphorescence, are uncovered. These distinctive features of the thiophene belts should inspire a range of applications such as optoelectronic devices and polar materials.
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issn 2041-1723
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publishDate 2025-02-01
publisher Nature Portfolio
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series Nature Communications
spelling doaj-art-13e7b261ad204224a4aa79141ba9b4882025-02-09T12:45:04ZengNature PortfolioNature Communications2041-17232025-02-011611910.1038/s41467-025-55896-wThiophene-fused aromatic beltsHiroki Shudo0Philipp Wiesener1Elena Kolodzeiski2Kiichi Mizukami3Daiki Imoto4Harry Mönig5Saeed Amirjalayer6Hirotoshi Sakamoto7Henning Klaasen8Bart Jan Ravoo9Nobuo Kimizuka10Akiko Yagi11Kenichiro Itami12Department of Chemistry, Graduate School of Science, Nagoya University; ChikusaInstitute of Physics, University of MünsterTUM School of Natural Sciences, Department of Chemistry, Technical University of MunichGraduate School of Engineering, Kyushu UniversityDepartment of Chemistry, Graduate School of Science, Nagoya University; ChikusaInstitute of Physics, University of MünsterInterdisciplinary Center for Scientific Computing, Heidelberg UniversityInstitute for Integrated Cell-Material Sciences (WPI-iCeMS), Kyoto UniversityOrganic Chemistry Institute, University of MünsterOrganic Chemistry Institute, University of MünsterGraduate School of Engineering, Kyushu UniversityDepartment of Chemistry, Graduate School of Science, Nagoya University; ChikusaInstitute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University; ChikusaAbstract Aromatic belts, ultrashort carbon nanotubes, and related structures, are emerging molecular entities in the fields of organic electronics and supramolecular chemistry owing to their structural rigidity, fully fused π-conjugation, and well-defined cavity. Synthesis of aromatic belts with embedded thiophene structures, which manifest significant optoelectronic and conductive properties, has not yet been achieved. Herein, we report the synthesis of thiophene-fused aromatic belts (thiophene belts) via one-step sulfur cross-linking reaction of partially fluorinated cycloparaphenylenes. Their structural features, including unidirectional columnar stacking with high dipole moment in crystals, two-dimensional layer assembly on metal surfaces, and photophysical properties, such as long-lifetime phosphorescence, are uncovered. These distinctive features of the thiophene belts should inspire a range of applications such as optoelectronic devices and polar materials.https://doi.org/10.1038/s41467-025-55896-w
spellingShingle Hiroki Shudo
Philipp Wiesener
Elena Kolodzeiski
Kiichi Mizukami
Daiki Imoto
Harry Mönig
Saeed Amirjalayer
Hirotoshi Sakamoto
Henning Klaasen
Bart Jan Ravoo
Nobuo Kimizuka
Akiko Yagi
Kenichiro Itami
Thiophene-fused aromatic belts
Nature Communications
title Thiophene-fused aromatic belts
title_full Thiophene-fused aromatic belts
title_fullStr Thiophene-fused aromatic belts
title_full_unstemmed Thiophene-fused aromatic belts
title_short Thiophene-fused aromatic belts
title_sort thiophene fused aromatic belts
url https://doi.org/10.1038/s41467-025-55896-w
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