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Conveniently Synthesized Butterfly‐Shaped Bitriphenylenes and their Application in Solution‐Processed Organic Field‐Effect Transistor Devices
Author(s) -
Ramakrishna Jagarapu,
Karunakaran Logesh,
Paneer Shyam Vinod Kumar,
Chennamkulam Ajith Mithun,
Subramanian Venkatesan,
Dutta Soumya,
Venkatakrishnan Parthasarathy
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901470
Subject(s) - triphenylene , stacking , chemistry , intermolecular force , graphane , absorption (acoustics) , thermal stability , electrochemistry , optoelectronics , photochemistry , molecule , organic chemistry , materials science , computational chemistry , density functional theory , electrode , composite material
Various π‐extended new bitriphenylene derivatives (both conformationally‐free and conformation‐locked) have been successfully synthesized by a facile Scholl oxidative cyclodehydrogenation method in good to excellent yields. Their optical properties in solution and film states reveal possibility for self‐ordering. The molecular packing in solid‐state demonstrates favorable π–π stacking as well as weak intermolecular interactions leading to face‐to‐face or slipped‐stack arrangements. Besides, these butterfly‐shaped large bitriphenylenes display near‐UV absorption, excellent photochemical, thermal, and electrochemical stabilities. The all‐organic anneal‐free transparent FETs fabricated from solution‐processable bitriphenylenes showcase significant improvement (ca. 4 orders of magnitude higher) in charge transporting abilities ( µ h : from ca. 10 –7 to 10 –3 cm 2 /(Vs)) when compared to model triphenylene. The fabricated FETs unveil excellent air stability (> 1 year under atmospheric conditions) highlighting the utility of these novel link‐locked triphenylene skeletons in organic electronics.