Premium
Stabilizing Two Classical Antiaromatic Frameworks: Demonstration of Photoacoustic Imaging and the Photothermal Effect in Metalla‐aromatics
Author(s) -
Zhu Congqing,
Yang Yuhui,
Luo Ming,
Yang Caixia,
Wu Jingjing,
Chen Lina,
Liu Gang,
Wen Tingbin,
Zhu Jun,
Xia Haiping
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201501349
Subject(s) - antiaromaticity , cyclobutadiene , pentalene , photoacoustic imaging in biomedicine , chemistry , photothermal therapy , photochemistry , molecule , materials science , computational chemistry , chemical physics , nanotechnology , organic chemistry , aromaticity , physics , optics
Antiaromatic species are substantially less thermodynamically stable than aromatic moieties. Herein, we report the stabilization of two classical antiaromatic frameworks, cyclobutadiene and pentalene, by introducing one metal fragment through the first [2+2] cycloaddition reaction of a late‐transition‐metal carbyne with alkynes. Experimental observations and theoretical calculations reveal that the metal fragment decreases the antiaromaticity in cyclobutadiene and pentalene simultaneously, leading to air‐ and moisture‐stable products. These molecules show broad absorption from the UV to the near‐IR region, resulting in photoacoustic and photothermal effects for metalla‐aromatic compounds for the first time. These results will encourage further efforts into the exploration of organometallic compounds for photoacoustic‐imaging‐guided photothermal therapy.