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Synthesis and Evaluation of a 1,3a,6a‐Triazapentalene (TAP)‐Bonded System
Author(s) -
Ito Masami,
Mera Akane,
Mashimo Takaki,
Seki Tomohiro,
Karanjit Sangita,
Ohashi Eisaku,
Nakayama Atsushi,
Kitamura Kei,
Hamura Toshiyuki,
Ito Hajime,
Namba Kosuke
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804733
Subject(s) - tap water , engineering , environmental engineering
A method of synthesizing a directly connected 1,3a,6a‐triazapentalene (TAP) ring system as a linearly bonded aromatic system with a planar form was established. Various TAP‐dimers and a 2‐alkyl‐TAP‐trimer were synthesized and their fluorescence properties were evaluated. Although the direct connection of the TAP ring with other TAP rings did not affect the fluorescence properties in diluted solvent, TAP‐dimers showed unique fluorescence properties derived from the aggregation state under highly concentrated conditions. In particular, TAP‐dimer 5 f showed aggregation‐induced emission in highly concentrated solution, and 5 b showed typical mechanochromic fluorescence in the solid state despite their compact molecular size.