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Engineering pH-responsive switching of donor-π-acceptor chromophore alignments along a peptide nanotube scaffold.

ABSTRACT: A cyclic tri-β-peptide cyclo(β-Ala-β-Ala-β-Lys) having diethylaminonaphthalimide at the β-Lys side chain (CP3Npi) self-assembled into a peptide nanotube in a solution of HFIP and water. CD spectra of the CP3Npi nanotubes show a negative Cotton effect at 441 nm and a positive Cotton effect at 393 nm, indicating that D-π-A naphthalimide chromophores are aligned in a left-handed chiral way along the nanotube. The CP3Npi nanotubes bear positive charges under acidic conditions retaining the nanotube structure but pH-responsive switching of D-π-A naphthalimide alignments along the nanotube between a left-handed chiral and random arrangement was observed. The peptide nanotube is a stable scaffold for attaining pH-responsive alignment switching of side-chain chromophores.

SUBMITTER: Tabata Y

PROVIDER: S-EPMC9048487 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Engineering pH-responsive switching of donor-π-acceptor chromophore alignments along a peptide nanotube scaffold.

Tabata Yuki Y Kamano Yusuke Y Kimura Shunsaku S Uji Hirotaka H

RSC advances 20200122 6

A cyclic tri-β-peptide cyclo(β-Ala-β-Ala-β-Lys) having diethylaminonaphthalimide at the β-Lys side chain (CP3Npi) self-assembled into a peptide nanotube in a solution of HFIP and water. CD spectra of the CP3Npi nanotubes show a negative Cotton effect at 441 nm and a positive Cotton effect at 393 nm, indicating that D-π-A naphthalimide chromophores are aligned in a left-handed chiral way along the nanotube. The CP3Npi nanotubes bear positive charges under acidic conditions retaining the nanotube ...[more]

PMID: 35497746

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Project description:Steady development on photophysical behaviors for a variety of organic fluorophores inspired us to generate anthracene-based fluorescent molecules with a strong acceptor and a significantly weak donor through a π-spacer. Such molecules are found to have substantial twisted conformational orientations in the solid state and enhanced apolar character because of the attachment of tolyl or mesityl group with an anthracenyl core. Upon exposure to a variety of solvents, strong solvatochromism was noticed for 4-nitro compound (84 nm red shift) in contrast to the cyano analogue (18 nm red shift). Both these probes were highly emissive in apolar solvents while nitro-analogue, in particular, could discriminate the solvents of E T(30) (a measure of microscopic solvent polarity) ranging from 31 to 37. Thus, 4-nitro compounds can be successfully employed to detect and differentiate the apolar solvents. On the contrary, the 2-nitro analogue is almost nonemissive for the same range of solvents perhaps because of favorable excited-state intramolecular proton-transfer process. The fundamental understanding of solvatochromic properties through the formation of twisted intramolecular charge-transfer (TICT) state is experimentally analyzed by synthesizing and studying the π-conjugates linked to only benzene in place of nitro or cyanobenzene, which exhibits no solvatochromism and that helped finding the possible emission, originated from the locally excited state. Moreover, the molecular structures for these compounds are determined by the single-crystal X-ray diffraction studies to examine the change in emission properties with molecular packing and alignment in the aggregated state. The measurement of dihedral angles between the substituents and anthracenyl core was helpful in finding the possible extent of electronic conjugations within the system to decipher both solvatochromism and aggregation enhanced emission (AEE)-behavior. The cyano analogue exhibited prominent AEE-behavior, whereas nitro analogues showed the aggregation-caused quenching effect. The reason behind such dissimilarity in solvatochromism and AEE-behavior between cyano- and nitro-linked anthracenyl π-conjugates are also addressed through experimental outcomes.

Dataset Information

Engineering pH-responsive switching of donor-π-acceptor chromophore alignments along a peptide nanotube scaffold.

Publications

Engineering pH-responsive switching of donor-π-acceptor chromophore alignments along a peptide nanotube scaffold.

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