Document Type

Thesis - University Access Only

Award Date


Degree Name

Master of Science (MS)

Department / School

Chemistry and Biochemistry


The photochemistry of two 1,8-naphthalimide derivatives, N-butyl-1,8- naphthalimide (HB) and N-butyl-4-butylamino-1,8-naphthalimide (44), were studied to determine their mechanism of photoactivity as related to tissue welding and viral inactivation. A mixture of the N-substituted derivative (HB) with n-butylamine shows formation of a charge transfer complex. The fluorescence emission spectrum of the 4- substituted derivative ( 44) shows a dual fluorescence nature characteristic of two distinct conformations. One is the normal, planar conformation, while the other is an anomalous, orthogonal conformation. The anomalous conformation has been related to the twisted internal charge transfer or TICT state. This state is highly polar and is favored in polar solvents. Irradiation of 44 leads to the formation of a fluorescent photoproduct. The fluorescent photoproduct appears to be HB, a second, non-fluorescent photoproduct is postulated to be n-butylimine. It is the second photoproduct which is reactive and suspected to be the initiator for the tissue welding properties of related 4-substituted naphthalimide derivatives.

Library of Congress Subject Headings

Dyes and dyeing -- Chemistry Photochemistry



Number of Pages



South Dakota State University