Triazoliptycenes: A Twist on Iptycene Chemistry for Regioselective Cross-Coupling To Build Nonstacking FluorophoresClick to copy article linkArticle link copied!
Abstract

Triazoliptycene fluorophores have been designed and synthesized, in which a three-dimensional propeller-like iptycene motif is employed to suppress intermolecular π–π stacking in the solid state. Key to the success of this modular synthesis is a stereoelectronic bias imposed by the iptycene scaffold, which assists the desired regioselectivity in the C–N cross-coupling step as the last-stage structure diversification from a common precursor.
Cited By
Smart citations by scite.ai include citation statements extracted from the full text of the citing article. The number of the statements may be higher than the number of citations provided by ACS Publications if one paper cites another multiple times or lower if scite has not yet processed some of the citing articles.
This article is cited by 15 publications.
- Heechan Kim, Younghun Kim, Dongwhan Lee. Small is Beautiful: Electronic Origin and Synthetic Evolution of Single-Benzene Fluorophores. Accounts of Chemical Research 2024, 57
(1)
, 140-152. https://doi.org/10.1021/acs.accounts.3c00605
- Hongsik Kim, Youngnam Lee, Hyeonho Lee, Jong-In Hong, Dongwhan Lee. Click-To-Twist Strategy To Build Blue-to-Green Emitters: Bulky Triazoles for Electronically Tunable and Thermally Activated Delayed Fluorescence. ACS Applied Materials & Interfaces 2021, 13
(10)
, 12286-12295. https://doi.org/10.1021/acsami.1c00278
- Frank S. Benneckendorf, Valentina Rohnacher, Eric Sauter, Sabina Hillebrandt, Maybritt Münch, Can Wang, Stefano Casalini, Katharina Ihrig, Sebastian Beck, Daniel Jänsch, Jan Freudenberg, Wolfram Jaegermann, Paolo Samorì, Annemarie Pucci, Uwe H. F. Bunz, Michael Zharnikov, Klaus Müllen. Tetrapodal Diazatriptycene Enforces Orthogonal Orientation in Self-Assembled Monolayers. ACS Applied Materials & Interfaces 2020, 12
(5)
, 6565-6572. https://doi.org/10.1021/acsami.9b16062
- Fabian Jester, Tobias Kaczun, Steffen Maier, Paul Meiners, Svenja Weigold, Frank Rominger, Andreas Dreuw, Jan Freudenberg, Uwe H. F. Bunz. Diels‐Alder Reactivity of Triisopropylsilyl Ethynyl Substituted Acenes. Chemistry – A European Journal 2025, 31
(2)
https://doi.org/10.1002/chem.202403522
- I. A. Lavrinchenko, T. D. Moseev, M. V. Varaksin, V. N. Charushin, O. N. Chupakhin. Luminophores based on 2H-1,2,3-triazoles: synthesis, photophysical properties, and application prospects. Russian Chemical Reviews 2024, 93
(10)
, RCR5130. https://doi.org/10.59761/RCR5130
- Sechan Lee, Giyun Kwon, Taewon Kang, Jihyeon Kim, Byungju Lee, Chunjoong Kim, Changsoo Lee, Youngsu Kim, Joohyeon Noh, Young-Sang Yu, Dongwhan Lee, Kisuk Kang. High-voltage (4.1 V) organic electrode material with an oxygen redox center. Journal of Materials Chemistry A 2023, 11
(41)
, 22441-22448. https://doi.org/10.1039/D3TA04373H
- Hongsik Kim, Hyejin Yoo, Jin Yeong Kim, Dongwhan Lee. A hydrogen-bonded organic framework of rigidly branched fluorophore: guest-adaptive cavity and phase-dependent light emission. Journal of Materials Chemistry C 2023, 11
(38)
, 12933-12940. https://doi.org/10.1039/D3TC01826A
- Zengye Gao, Yue Wang, Yang Zhou, Bingxin Yuan, Zheng Duan. Synthesis and properties of photoluminescent phosphorus-doped triptycenes. Dalton Transactions 2023, 52
(33)
, 11390-11394. https://doi.org/10.1039/D3DT02308G
- Yuichiro Tokoro, Genta Nakayama, Shin‐ichi Yamamoto, Toshio Koizumi. Tuning Solid‐State Emission Behavior of Janus‐Type Anthracenes by Addition of Shielding Bridges. ChemPhotoChem 2022, 6
(9)
https://doi.org/10.1002/cptc.202200074
- Taewon Kang, Hongsik Kim, Sungeun Jeoung, Dohyun Moon, Hoi Ri Moon, Dongwhan Lee. Non-stackable molecules assemble into porous crystals displaying concerted cavity-changing motions. Chemical Science 2021, 12
(18)
, 6378-6384. https://doi.org/10.1039/D1SC01163D
- Chun‐Wei Chiu, Jye‐Shane Yang. Photoluminescent and Photoresponsive Iptycene‐Incorporated π‐Conjugated Systems: Fundamentals and Applications. ChemPhotoChem 2020, 4
(8)
, 538-563. https://doi.org/10.1002/cptc.201900300
- Stephanie Montanaro, Daniel G. Congrave, Marc K. Etherington, Iain A. Wright. Homoconjugation enhances the photophysical and electrochemical properties of a new 3D intramolecular charge transfer iptycene displaying deep blue emission. Journal of Materials Chemistry C 2019, 7
(41)
, 12886-12890. https://doi.org/10.1039/C9TC03255J
- Yuanxiang Li, Sufang Lei, Yilin Liu. Design, Synthesis and Fungicidal Activities of Novel 1,2,3‐Triazole Functionalized Strobilurins. ChemistrySelect 2019, 4
(3)
, 1015-1018. https://doi.org/10.1002/slct.201803597
- Chuanxin Zhang, Lei Zheng, Qiong Yan, Qinquan Hu, Fengcheng Jia, Yunfeng Chen. A Direct P
2
O
5
‐Mediated Synthesis of Diverse Sulfur‐Containing Triazoles
via
Alkylation of
NH
‐1,2,3‐triazoles with Dimethyl Sulfoxide. ChemistrySelect 2018, 3
(37)
, 10277-10280. https://doi.org/10.1002/slct.201802875
- Bassam Alameddine, Noorullah Baig, Suchetha Shetty, Saleh Al‐Mousawi, Fakhreia Al‐Sagheer. Tuning the optical properties of ethynylene triptycene‐based copolymers via oxidation of their alkyne groups into α‐diketones. Journal of Polymer Science Part A: Polymer Chemistry 2018, 56
(8)
, 931-937. https://doi.org/10.1002/pola.28971
Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.
Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.
The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.