Bisindeno-annulated pentacenes with exceptionally high photo-stability and ordered molecular packing: simple synthesis by a regio-selective Scholl reaction

• Published in: Chemical communications (Cambridge, England) Vol. 51; no. 17; pp. 3604 - 3607
• Main Authors: Naibi Lakshminarayana, Arun, Chang, Jingjing, Luo, Jie, Zheng, Bin, Huang, Kuo-Wei, Chi, Chunyan
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 28.02.2015
• Subjects: Access control; air; chemical compounds; chemical reactions; Chemistry; Chemistry, Multidisciplinary; crystals; Half life; Pentacene; Physical Sciences; Precursors; Science & Technology; Single crystals; Stacking; Strategy; Synthesis (chemistry); ACENES; HEPTACENE; RUBICENES; POLYCYCLIC AROMATIC-HYDROCARBONS; ELECTRONICS; HEXACENE
• ISSN: 1359-7345; 1364-548X; 1364-548X
• DOI: 10.1039/C4CC09812A

Bisindeno-annulated pentacenes 3a and 3b were synthesized by a simple regio-selective, FeCl 3 -mediated Scholl reaction from the corresponding 6,13-diaryl pentacene precursors. The fusion of two indeno-units dramatically changes the electronic properties and chemical reactivity of pentacene and the obtained compounds exhibited exceptionally high photo-stability in the solution, with a half-life time of 11.2 ( 3a ) and 32.0 ( 3b ) days under ambient light and air conditions. Ordered molecular packing with a small π–π stacking distance was observed in the single crystals of 3a and 3b . Our research provides a promising strategy to access stable higher order acenes with controlled molecular order.