We study the effect
of molecular conformation on the electronic
coupling between the donor amines and acceptor 1,8-naphthalimide
(NPI) in a series of D–A systems 1–4 (A = NPI; D = phenothiazine, phenoxazine, carbazole, diphenylamine,
respectively, for 1, 2, 3,
and 4). Weakly coupled systems show dual emission in
the solution state, while strongly coupled systems show single emission
bands. The energy of transitions and photoluminescence (PL) quantum
yield are sensitive to the molecular conformation and donor strength.
These compounds show delayed emission in the solutions and aggregated
state and phosphorescence in the solid state. Compounds 3 and 4 with weak donors exhibit intermolecular slipped
π···π interactions in the solid state and
consequently exhibit dual (intra- and inter-) phosphorescence at low
temperature. Steady state and time-resolved PL studies at variable
temperature together with computational and crystal structure analysis
were used to rationalize the optical properties of these compounds.
The delayed emission of these compounds is sensitive to molecular
oxygen; accordingly, these molecules are utilized for differential
imaging of normoxia and hypoxia cancer cells.