In this work, nitrogen-annulated perylene (NP) was dimerized into one framework connected by two nitrogen atoms, generating the target molecule of DNP-DA. Owing to the substructure of 1,6-diazecine ten-membered ring, DNP-DA illustrates helical chirality with moderate dissymmetry factor, elevated molecular levels, expanded conjugation and supramolecular interactions with acceptors etc. Notably, DNP-DA represents a limited example of nitrogen-perylene based CPL emitter with g around 6×10 . Intrigued by the facile fabrication via a simple amination-cross coupling sequence and other above advancing features, this work demonstrates the potential generality of utilizing 1,6-diazecine as a chiral unit to build CPL-active materials.
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http://dx.doi.org/10.1002/chem.202203550 | DOI Listing |
Phys Chem Chem Phys
October 2023
School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram (IISER TVM), Vithura, Thiruvananthapuram, Kerala, 695551, India.
The efficient population of the triplet excited states in heavy metal-free organic chromophores has been one of the long-standing research problems to molecular photochemists. The negligible spin-orbit coupling matrix elements in the purely organic chromophores and the large singlet-triplet energy gap (Δ) pose a hurdle for ultrafast intersystem crossing (ISC). Herein we report the unprecedented population of triplet manifold in a series of nitrogen-annulated perylene bisimide chromophores (NPBI and Br-NPBI).
View Article and Find Full Text PDFChemistry
April 2023
School of Chemistry and Chemical Engineering, Inner Mongolia University, 235 West University Street, Hohhot, 010021, China.
In this work, nitrogen-annulated perylene (NP) was dimerized into one framework connected by two nitrogen atoms, generating the target molecule of DNP-DA. Owing to the substructure of 1,6-diazecine ten-membered ring, DNP-DA illustrates helical chirality with moderate dissymmetry factor, elevated molecular levels, expanded conjugation and supramolecular interactions with acceptors etc. Notably, DNP-DA represents a limited example of nitrogen-perylene based CPL emitter with g around 6×10 .
View Article and Find Full Text PDFChem Asian J
August 2022
School of Chemistry and Chemical Engineering, Inner Mongolia University, 235 West University Street, Hohhot, 010021, P. R. China.
A B-N embedded nitrogen-annulated perylene has been successfully synthesized. The resultant molecule BN-NP is isoelectronic to coronene, but owns a five-membered pyrrole ring. Experiments and DFT calculations indicated that peripheral pyrrole and BN modifications endow BN-NP with various unique properties like bent structure, dual emission, efficient Lewis acidic response, peripheral aromaticity, narrowest energy band gap among all coronene isoelectronic structures and so on.
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